Location: Maitland , 32751
Do Not Show Listings
1140 S ORLANDO AVE #H3, MAITLAND, FL 32751
$439,90020 Days on yellowkey MLS ID: O6415783
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 816 Built: 1964Monthly Fee: $546 Tax: $2,530 (2025)Community: Lake Maitland Terrace AptsCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,530
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: 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!
Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)
Listing Agent: Christopher Schiffermiller, Llc (407-409-5702)
206 MOSELEY AVE, MAITLAND, FL 32751
$449,00033 Days on yellowkey MLS ID: O6414097
0 Days Off yellowkey (back on 6/18/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1838 Built: 2026 Tax: $3,007 (2025)Community: Pindar SubSingle Family
Taxes:$3,007
Elementary School: Hungerford Elem
High School: Edgewater High
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. Inside, the home opens into a bright and airy open-concept living space highlighted by high tray ceilings, recessed lighting, oversized glossy tile flooring, and an abundance of natural light. The seamless flow between the living, dining, and kitchen areas creates the perfect setting for both entertaining and everyday luxury living.
Listing is courtesy of: SYCHAR REALTY (407-921-0069)
Listing Agent: Brianna Grant (407-764-8436)
873 CRANES CT, MAITLAND, FL 32751
$1,224,900100 Days on yellowkey MLS ID: O6394418
REDUCED by $25,000 (2.0%) on 06/18/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3902 Built: 1996Monthly Fee: $199 Tax: $9,081 (2025)Community: Lake Sybelia Cove Ph 01Single Family
Taxes:$9,081
Elementary School: Lake Sybelia Elem
Remarks: Beautifully Maintained Original-Owner Pool Home in Gated Lake Sybelia Cove. 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.
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Chris Creegan (407-622-1111)
910 GAMEWELL AVE, MAITLAND, FL 32751
$645,00061 Days on yellowkey MLS ID: O6404438
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: 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 is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Sarah Tomlinson (407-721-7823)
570 DOMMERICH DR, MAITLAND, FL 32751
$795,000132 Days on yellowkey MLS ID: O6377363
0 Days Off yellowkey (back on 6/17/2026)
REDUCED by $80,000 (9.1%) on 06/13/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2956 Built: 1963 Tax: $5,529 (2024)Community: Dommerich Estates 2Nd AddSpa: NoSingle Family
Taxes:$5,529
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Virtually Staged. ONE OF A KIND for Dommerich Estates, this LAKE VIEW Home is designed for soaking in unforgettable sunsets and unwinding after a long day. Located directly across the street from the neighborhood lake lot, you will enjoy unobstructed views of the water, easy access to the boat ramp and fishing dock or launch your canoe or kayak for a peaceful paddle on the lake that also connects to the Winter Park Chain of Lakes! 4 generous bedrooms and 3 baths provide plenty of space for family and guests. Beautiful wood floors flow throughout and are complemented by crown molding for a classic touch. The spacious living room has a wood-burning fireplace and built-in cabinets to display all your treasures. It’s also large enough to be used for a combination living room/dining room and enjoy the lake views while you dine. The open kitchen and family room look out onto the screened patio and pool with a relaxing water feature. Feel secure during hurricane season with an installed and powerful Briggs and Stratton generator that will keep the power going to the kitchen, 4th bedroom and bath during the storm! Upgraded electrical system and the home has been replumbed for your peace of mind. Dommerich Estates has a strong sense of community and was designed and built around A rated schools so walking and biking to school is safe and easy. Social events at the lake lot provide a fun opportunity for neighbors to meet neighbors and there is a boardwalk that connects you to Maitland Park with playgrounds, tennis courts, walking trails and basketball courts. The City of Maitland is vibrant with a small-town feel providing events designed to foster connections among residents with multiple parks and downtown events and concerts! Don’t pass on this opportunity to own this rare, lake view home in one of the best neighborhoods in the area!
Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)
Listing Agent: Shirley Welch (407-718-1450)
908 VERSAILLES CIR, MAITLAND, FL 32751
$899,00033 Days on yellowkey MLS ID: O6413200
2 Days Off yellowkey (back on 6/17/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2151 Built: 1979 Tax: $11,362 (2025)Community: VersaillesSingle Family
Taxes:$11,362
Remarks: Under contract-accepting backup offers. Ideally in one of Maitland’s desired neighborhoods, Versailles, this fully renovated home blends timeless architecture with modern comfort. With sun-filled interiors, an open-concept layout, a serene primary suite and freshly landscaped grounds, every detail supports effortless living. This three-bed, two-bath home stretches over 2,151 square feet and is situated on 0.29 of an acre. This classic ranch style offers a split bedroom plan with endless function. A gracious foyer welcomes you into this serene space with blonde oak flooring, limewash accent walls, a vaulted ceiling with wood beam accents, fresh neutral tones, designer fixtures and ambient lighting that softens the spaces. This home features formal dining and a flex space that could be a fourth bedroom or office, offering many layout choices. The combined kitchen and living room showcases a wood-burning fireplace with a fluted marble surround as the focal point. The kitchen combines crisp, clean-lined cabinets and warm-wood-toned floor-to-ceiling storage cabinets finished with brushed-gold hardware. A waterfall center island with quartz counters that continue up the backsplash for a stylish design. Clear view sliders open to a covered porch with a tongue and groove ceiling feature and is part of a screened pool, making entertaining a breeze. Recently installed turf grass for ease of maintenance and keeps it all looking very fresh. The pool was recently refinished and a side-yard sauna rounds out this oasis. The primary suite is a private retreat with an oversized walk-in shower with beautiful vertical Zellige tile. Dual vanities with custom arched mirrors, sconce lighting and porcelain-marble floors add to the space. Built-in linen closets and dual bedroom closets make organization simple. Additional highlights include both baths completely renovated, new kitchen appliances (LG/GE stainless steel) induction range, new interior doors and hardware, new ceiling fans, new Pella front doors and Impervia slider doors across the back of the home, new Pella front windows, a new Hass garage door (2025), the whole yard professionally designed and landscaped (2026), a sauna (2024), a roof (approximately 2018) and a water heater (2023). This neighborhood enjoys a community lake lot with access to Lake Minnehaha, part of the Winter Park lake chain. Strategic location close to major roadways, short distance to the Sunrail and close to all amenities that make Maitland special. Zoned for some of the best Orange County schools: Lake Sybelia, Maitland Middle and Winter Park High, a nationally renowned school for its International Baccalaureate Program.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
1781 TONTO TRL, MAITLAND, FL 32751
$600,00026 Days on yellowkey MLS ID: O6414036
1 Days Off yellowkey (back on 6/17/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1880 Built: 1968Monthly Fee: $17 Tax: $2,220 (2025)Community: Dommerich Estates 1St AddSingle Family
Taxes:$2,220
Remarks: Under contract-accepting backup offers. Welcome to 1781 Tonto Trail, a 4-bedroom home in one of Maitland's most desirable neighborhoods, offering just under 1,900 square feet of living space, a split bedroom floor plan, and access to the Winter Park Chain of Lakes. Located on a corner lot just under a quarter acre, this move-in ready residence combines functionality, comfort, and an exceptional Maitland location. Inside, you'll find a formal living room and formal dining room that provide flexible spaces for entertaining, working from home, or everyday living. The spacious family room serves as a central gathering area and connects seamlessly to the home's thoughtful layout. The private primary suite features an ensuite bathroom and double closets, creating a comfortable retreat. Bedrooms two and three offer large walk-in closets, providing abundant storage and flexibility for family, guests, or home office needs. The split bedroom design enhances privacy while maintaining a practical flow throughout the home. Residents of Dommerich Estates enjoy access to highly regarded schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. A voluntary low-cost HOA provides access to a private boat ramp on the Winter Park Chain of Lakes, creating opportunities for boating, fishing, paddleboarding, and waterfront recreation. The location places you short distance to the Maitland Community Park, Maitland Social, and Maitland City Centre, offering convenient access to local dining, recreation, events, and community amenities. Whether you're looking for more space, access to top-rated schools, or the lifestyle benefits of a lake-access community, this 4-bed home in Dommerich Estates delivers a rare opportunity to enjoy one of Maitland's most established and sought-after neighborhoods.
Listing is courtesy of: EXP REALTY LLC (407-641-2808)
Listing Agent: Todd Schroth, Pa (407-641-2808)
204 QUAYSIDE CIR #201, MAITLAND, FL 32751
$467,00082 Days on yellowkey MLS ID: O6394791
REDUCED by $15,000 (3.1%) on 06/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1270 Built: 1984 Tax: $6,566 (2025)Community: Moorings On Lake Maitland CondoCondo
Taxes:$6,566
Remarks: Updated 2 bedroom 2 bathroom located on the second floor of sought after Moorings Lakefront Community with spectacular views of Lake Maitland of the Winter Park Chain of Lakes. The condo offers a large screened-in balcony overlooking Lake Maitland. The open floorpan offers a split plan with a generous size master retreat with a private door to the balcony and a secondary ensuite. The updated spacious kitchen features stainless steel appliances and a breakfast nook situated in a bay window. The dining living room combo is very spacious making it perfect for relaxing or entertaining. The condo offers washer and dryer in the unit as well as a private storage closet on the same floor just across the hall. The Moorings Lakefront community offers an amazing recently updated pool and spa area along a large clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this condo and community offers an amazing combination of comfort and convenience.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Angel Reyes (407-697-3313)
1400 LAKE SHADOW CIR #10103, MAITLAND, FL 32751
$155,00082 Days on yellowkey MLS ID: S5147962
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 672 Built: 2000 Tax: $2,238 (2025)Community: Visconti West CondoCondo
Taxes:$2,238
Remarks: Nice one-bedroom unit on the ground floor featuring brand-new laminate countertops in both the kitchen and bathroom, along with stainless steel appliances. Located in a gated, resort-style community offering top amenities including a pool, fitness center, tennis and basketball courts, playground, clubroom, and car wash. All in an excellent Maitland location!
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Gilgra Valduz Sandoval (321-310-3259)
1440 LAKE SHADOW CIR #8201, MAITLAND, FL 32751
$199,00025 Days on yellowkey MLS ID: O6416664
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1111 Built: 2000Monthly Fee: $532 Tax: $3,298 (2025)Community: Visconti West CondoCondo
Taxes:$3,298
Middle School: Lockhart Middle
Remarks: If you are looking for a terrific property, look no further! You or your tenant can live the lifestyle deserved in this RESORT-STYLE, video-monitored GATED COMMUNITY located on beautiful Lake Shadow in the heart of Maitland Center. This two-bed/two-bath, 2nd-story, CORNER UNIT features an OPEN floor plan with a LIVING/DINING COMBO and 9-FOOT CEILINGS. The KITCHEN includes a breakfast bar, closet pantry, INSIDE UTILITY CLOSET with washer and dryer, and neutral tile. All appliances convey at closing. DOUBLE MASTERS each offer an en-suite bath and a walk-in closet. The 20 X 20 living area provides lots of sunlight and features a built-in nook with glass shelving you can use as you choose. In 2024, the interior was painted, and carpet was installed. Through sliders, you can unwind at the end of a busy day on the SCREEN-ENCLOSED tiled LANAI and enjoy a TRUE ESCAPE. If extra storage is needed, a patio closet awaits! This GORGEOUSLY LANDSCAPED and PET-FRIENDLY community offers two LAKESIDE POOLS with Wi-Fi access, a club-quality FITNESS CENTER, grand CLUB ROOM with CATERING KITCHEN, fully-equipped BUSINESS CENTER, lighted TENNIS courts, BASKETBALL court, car wash area, two laundry facilities, 24-HOUR MAINTENANCE, WATER, SEWER, and a Monday-Friday VALET WASTE REMOVAL SERVICE. The condo community boasts a newer tile roof, reflecting ongoing care and investment in the property. Located minutes away from SR 414, I-4, 429, Routes 434 and 436; it is a quick drive to downtown Orlando, Cranes Roost Park, and to the upscale shopping and dining at Altamonte Mall, Altamonte Towne Center, Winter Park Village, and Winter Park’s quaint Park Avenue. Enjoy Florida living at its best! This property may be under audio & visual surveillance.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Susan Schneider (407-461-1150)
1106 CHARMING ST, MAITLAND, FL 32751
$490,00034 Days on yellowkey MLS ID: O6413431
0 Days Off yellowkey (back on 6/15/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1870 Built: 2006Monthly Fee: $520 Tax: $6,232 (2025)Community: Enclave/Maitland A-FSpa: NoTownhouse
Taxes:$6,232
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained lakefront townhome in a highly desirable gated community in Maitland with almost 1900 square feet of thoughtfully designed living space. This 3-bedroom, 2.5-bath residence combines comfort, functionality, and picturesque lake views. Enjoy serene views of Lake Charity from the charming front porch, formal dining room, and two upstairs bedrooms. Soaring ceilings and abundant natural light create an airy, inviting atmosphere throughout the home. The spacious open-concept kitchen overlooks the family room and features ample counter seating for barstools, generous cabinetry, and a nice pantry. A private courtyard provides a welcoming outdoor retreat and leads to the oversized 2-car garage with abundant attic storage above. The separate dining room offers a perfect setting for entertaining while enjoying tranquil lake views. A convenient guest bathroom is located on the first floor as well. Upstairs, the massive Primary suite serves as a true retreat, featuring a custom walk-in closet and a spa-inspired en-suite bath with a soaking tub, separate shower, and dual vanities. Two additional bedrooms have stunning views of the lake. One includes a Murphy bed with beautiful built-ins and a custom closet. Another full bath, and a spacious laundry room with plenty of storage complete the second floor. The reasonable HOA fee includes use of the sparkling pool, the secure gate, all landscaping, all maintenance of the exterior of this townhome including the roof, repairs, and paint, and high-speed internet with cable TV, through Spectrum. Offering exceptional space, beautiful water views, and a sought-after gated location, this townhome is the ideal place to call home. *A complimentary complete one-year Home Warranty is provided for extra peace of mind. (A recent Lender's appraisal is also available.)
Listing Agent: Donna Bryant (407-509-8047)
830 LONGHAVEN DR, MAITLAND, FL 32751
$675,00028 Days on yellowkey MLS ID: O6414213
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2229 Built: 1964 Tax: $5,520 (2025)Community: Highland Park Estates First AddSingle Family
Taxes:$5,520
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 3 bedroom, 2 bath pool home offering 2,229 square feet of living space in the highly sought-after Dommerich neighborhood of Maitland. The heart of the home is the spacious kitchen featuring knotty pine cabinetry, granite countertops, a gas range, stainless steel appliances, a breakfast bar, and an elegant tray ceiling. The kitchen opens seamlessly to the family room, where a stunning brick accent wall showcases a cozy fireplace and a unique alcove perfect for indoor grilling and entertaining. A separate living room offers additional gathering space with its own fireplace and custom built-in bookshelves. The formal dining room is highlighted by a beautiful chandelier. French doors lead you to a spacious bonus room built in 2025, which is filled with natural light from new windows, providing endless possibilities for a home office, playroom, or flex space. Step outside to your private backyard retreat featuring a sparkling 10-foot-deep pool surrounded by classic herringbone-style pavers, creating the perfect setting for relaxation and outdoor entertaining. An outdoor storage shed provides added convenience. Recent updates include a brand-new roof (2026), newer windows, attractive wood shutters throughout, AC (2015), and water heater (2015) and indoor laundry room. Located within the highly acclaimed Dommerich Elementary, Maitland Middle, and Winter Park High School districts, this home offers the perfect blend of character, comfort, and location—don't miss this rare opportunity to make it yours.
Listing Agent: Ingrid Livingston (407-595-5972)
255 W GEORGE AVE, MAITLAND, FL 32751
$1,499,00026 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.
2401 LEGACY LAKE DR #2401, MAITLAND, FL 32751
$355,00034 Days on yellowkey MLS ID: O6412788
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1707 Built: 2000Monthly Fee: $589 Tax: $2,250 (2025)Community: Visconti EastCondo
Taxes:$2,250
Remarks: All roads lead to Visconti East! Located in Maitland, bordering nearby scenic Winter Park (Park Ave./ Rollins College) this distinctive 3 story, 4 Bed/2.5 Bath townhome is situated directly off of I-4 and SR414, within 10 minutes to Downtown Orlando, Park Avenue, and close access to SR429, Winter Garden, and North Orlando. This home offers a one-of-a-kind floor plan with the entry foyer, hall closet, half bath and uniquely set up two car garage on the first floor, living room/kitchen + primary bedroom/bath on the second floor, and 3 bedrooms/ full bathroom, large hallway closet on the third level. All bedrooms feature spacious walk-in closets. Situated next to two fountain ponds that are overlooked from both sides of the unit on 2nd/3rd floors. No need to worry about additional projects, this very special and unique townhouse is move-in ready with top-quality updated features and architectural design, including imported Bianca Antico granite countertops, Italian travertine flooring and showers, stylish arches, and a massive built in bookcase. Shopping, Entertainment and Major Retail are all within miles, including downtown Maitland and Winter Park Village. Premier luxury gyms Genesis Health Club and Lifetime Fitness minutes away for ice skating, pickleball, aquatics and wellness community. Beautiful and safe bike trails accessible just by a short walk/ride. Come see all that this home and community has to offer! Call today for your private showing!
Listing Agent: Trace Christian, Iii (407-202-8135)
1191 WILLOWBROOK TRL, MAITLAND, FL 32751
$765,00041 Days on yellowkey MLS ID: O6410813
0 Days Off yellowkey (back on 6/11/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2287 Built: 1966 Tax: $4,636 (2025)Community: Maitland WoodsSpa: NoSingle Family
Taxes:$4,636
Remarks: Under contract-accepting backup offers. Don't miss this rare opportunity to purchase your dream home in the established Maitland Woods neighborhood. This charming 4-bedroom, 2-bath home has been meticulously maintained and contains premium finishes throughout. The open floor plan includes a large family/great room, dining room, and an enclosed patio, perfect for entertaining. The updated kitchen features a handmade subway tile backsplash, quartzite countertops, stainless steel appliances, a coffee bar, and a versatile indoor laundry/ second office or crafting room. The primary bathroom has been completely renovated, with a double-sink marble vanity, large shower, and walk-in closet. The second full bathroom is centrally located, with additional access to the enclosed patio, making it also an optional (future) pool bath. This home includes a large (0.29-acre) fully fenced backyard, ideal for children and/or pets to play. Some notable exterior improvements include: a new front brick patio, a new firepit area for entertaining, a vegetable/flower garden and beautiful landscaping. Maitland Woods is conveniently located near I-4, making commuting to either downtown Orlando or Lake Mary a breeze. In addition, the home is within walking distance to Orangewood Christian School, Lake Sybelia Elementary, the shops and restaurants of downtown Maitland (home of a weekly farmer’s market), city events at Lake Lily, and Lake Sybelia’s very own Homer Hough Park. Homer Hough Park is the area’s best-kept secret, with a playground, fishing, and pavilions for family events. This home will not last, call to schedule your private showing today! Age of major components includes water heater 2022; NEW front patio 2026; roof 2016; HVAC 2024/2025; Replumb CPVC 2020; inside and outside electrical panels 2025; and double-pane windows 2016-2023 – with lifetime warranty.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Marti Hornell (407-222-1443)
2450 DERBYSHIRE RD, MAITLAND, FL 32751
$715,00055 Days on yellowkey MLS ID: O6407991
0 Days Off yellowkey (back on 6/9/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2245 Built: 1964 Tax: $6,941 (2025)Community: English Estates Unit 2Single Family
Taxes:$6,941
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: South Seminole Middle
Remarks: Under contract-accepting backup offers. Located in the highly desirable English Estates community, this beautifully renovated home blends modern updates with comfortable Florida living. Thoughtfully redesigned throughout, the home offers four spacious bedrooms and updated bathrooms, including a private primary suite featuring a spa-inspired bath and a custom walk-in closet with built-in shelving and organization. The open-concept kitchen flows seamlessly into the main living and dining areas and features quartz countertops, custom shaker cabinetry, stainless steel appliances, and an oversized peninsula ideal for everyday living and entertaining. Additional upgrades throughout the home include marble accents, upgraded recessed lighting, and a double-sided fireplace that adds warmth and character to the main living spaces. Large windows, including a custom back door slider, oversized aquarium-style window, and expansive kitchen window, bring in abundant natural light and overlook the backyard and pool area. Outside, the private backyard retreat is designed for both relaxing and entertaining, complete with a resort-style pool, updated coping, a new energy-efficient pool pump, custom fencing, and a brand-new paver pool deck. Situated on nearly half an acre and just minutes from the shops, restaurants, and parks of Winter Park, this home offers a great combination of style, privacy, and location.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Kyle Grafton (203-246-8512)
747 N LAKE SYBELIA DR, MAITLAND, FL 32751
$3,895,00057 Days on yellowkey MLS ID: O6406879
5 Days Off yellowkey (back on 6/9/2026)
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 5347 Built: 2023 Tax: $23,099 (2025)Community: Sybelia Shores Second AddSpa: YesSingle Family
Taxes:$23,099
Remarks: Under contract-accepting backup offers. Welcome to 747 N Lake Sybelia Drive, an extraordinary lakefront estate gracefully positioned along the desired northern shoreline of beautiful Lake Sybelia. Completed in late 2023, this breathtaking California Coastal-inspired residence spans 4,755 square feet on an expansive 0.76-acre homesite, blending timeless architecture with refined finishes to create a lifestyle defined by elegance, comfort and effortless lakefront living. Ideally situated on a gently sloping lot, the home captures stunning elevated views of the water, offering a rare sense of privacy, tranquility and perspective. Thoughtfully designed interiors are filled with natural light and crafted for everyday living and exceptional entertaining. The main level showcases a beautifully appointed chef’s kitchen anchored by an oversized island and complemented by a spacious walk-in butler’s pantry. Open-concept dining and living spaces are framed by picturesque lake views, while the expansive great room seamlessly connects indoor and outdoor living. A private office, guest suite and dedicated pool bath complete the first floor. Upstairs, a versatile loft and homework nook provide flexible living space, while two en-suite bedrooms and a serene primary retreat offer exceptional comfort and privacy. The luxurious primary suite and one secondary bedroom open to a spacious lakeside balcony, an idyllic place to enjoy morning coffee, evening sunsets and sweeping water views. Exceptional outdoor living spaces surround the home. A welcoming covered front porch offers the perfect vantage point to enjoy lake views and watch boating activity, while the expansive rear covered lanai is designed for year-round entertaining with a summer kitchen and generous space for lounging and dining. Overlooking the beautifully landscaped backyard, complete with bamboo-lined fencing for privacy, is a sparkling saltwater pool and spa by Titan Pools, thoughtfully designed for resort-style enjoyment and capable of both gas and electric heating. Uniquely embraced by water and recreation, the home enjoys tranquil lake vistas to the south and the stunning pool retreat to the north. The waterfront experience is elevated by a newly constructed composite dock with a heavy-duty dual-motor lift, while a thoughtfully designed shell-base boat ramp provides seamless, eco-conscious access for launching watercraft directly from your property. Adding even more versatility, a 500+ square-foot unfinished bonus room above the garage offers incredible potential for customization, ideal for a media room, guest retreat, fitness studio or creative space. Plumbing has been extended for a future bath or bar, and the space is currently enjoyed as a golf simulator. Car enthusiasts will appreciate the impressive four-car tandem garage featuring soaring 15-foot ceilings designed to accommodate vehicle lifts, premium wall-mounted jackshaft openers for maximum overhead clearance and a separate side-access bay ideal for golf cart storage. Engineered for longevity as much as luxury, the home features an extensive stormwater drainage system with hard-piped gutters designed to protect the land and prevent erosion. Ideally located, enjoy a short visit or golf cart ride to Maitland City Centre and Homer Hough Park at Sybelia Point, while the shopping and dining of Park Avenue are just minutes away. Convenient access to Interstate 4 and express lanes ensures effortless travel throughout the greater Orlando area.
Listing Agent: Mick Night (407-629-4446)
2697 QUEEN MARY PL, MAITLAND, FL 32751
$520,00040 Days on yellowkey MLS ID: O6411521
1 Days Off yellowkey (back on 6/9/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1558 Built: 1996Monthly Fee: $79 Tax: $7,441 (2025)Community: Brittany GardensSingle Family
Taxes:$7,441
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This gem is situated in the Brittney Gardens gated neighborhood in desirable Maitland. When you enter the home you are greeted by beautiful, rich wood floors and loads of natural light. The dining room flows seamlessly into the kitchen for ease when entertaining. The kitchen boasts quartz countertops, stainless-steel appliances, ample cabinet and counter space, breakfast bar & closet pantry. The kitchen overlooks the living room, which provides glass doors, complete with retractable screens, leading to the screened-in patio. The primary bedroom is a true private retreat and is on the opposite side of the home from the secondary bedrooms. The primary retreat includes a walk-in closet with a closet system and a spa-like ensuite bathroom with a dual sink vanity. The secondary bedrooms are across the home and share a hallway bathroom. The screened-in patio overlooks a rear paver patio which provides the perfect outdoor space to enjoy the Florida lifestyle. Other amenities and updates include a whole house generator, recently repainted interior, LED lights, new carpet in all the bedrooms, and a new tankless water heater. HVAC was installed in 2024. This home is close to several restaurants and shops and is just a short distance from both the newer Maitland City Center and famed Park Avenue in Winter Park. Welcome Home!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Beth Logullo (772-633-0670)
1393 BENEVOLENT ST, MAITLAND, FL 32751
$379,00083 Days on yellowkey MLS ID: O6399560
0 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1674 Built: 2005Monthly Fee: $520 Tax: $3,322 (2025)Community: Enclave/Maitland A-FTownhouse
Taxes:$3,322
Remarks: This beautiful Maitland Florida town home feels like living in a gated resort! 3 bedrooms, 2 1/2 baths, plus garage and loaded with upgrades including hardwood floors on both levels, crown molding, tall wood cabinets, stone counters and so much more. Welcoming entry foyer with half bath, kitchen with island sink, large breakfast bar, stainless appliances, granite counters and custom backsplash. Inviting living room and dining area offer plenty of space for entertaining, french door opens to private covered porch which overlooks the rear yard. Upstairs the ensuite primary bedroom has a walk-in closet, great covered balcony area and a dual sink bathroom with glass enclosed shower. Additional 2 bedrooms in the front of the upstairs share a hall bath and laundry closet with washer and dryer included. Montacino is a gated European feeling award winning community with amazing pool area, lake frontage and a convenient location to shopping and i4. This townhouse has a quiet location within the community offering privacy in the back area. All exterior maintenance is included (roof and paint too)! HOA dues include new fiber with internet and channel package and all Montacino amenities.
Listing is courtesy of: RENCHER REALTY GROUP (321-325-2040)
Listing Agent: Daniel Rencher (407-279-1946)
457 FORESTWOOD LN, MAITLAND, FL 32751
$849,00049 Days on yellowkey MLS ID: O6409383
5 Days Off yellowkey (back on 6/5/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2610 Built: 1978Monthly Fee: $33 Tax: $8,237 (2025)Community: StonewoodSingle Family
Taxes:$8,237
Elementary School: Lake Orienta Elementary
High School: Lyman High
Middle School: Milwee Middle
Remarks: Under contract-accepting backup offers. From the moment you step inside, you’re welcomed by a stunning double-sided fireplace and a sought-after conversation pit — the perfect setting to unwind with your favorite vinyl record, a glass of wine, and great company. Beyond the fireplace, the home opens into an expansive open-concept living space designed for both everyday comfort and effortless entertaining. The chef-inspired kitchen is the centerpiece of the home, featuring premium Forno appliances, a massive 11-foot island with seating for six, and a 6-burner Forno gas range with electric oven. Vaulted ceilings enhance the sense of space, while thoughtful details like the pot filler, apron sink, designer backsplash, and elegant cabinet hardware elevate the entire experience. Adjacent to the kitchen, the butler’s pantry offers butcher block countertops, abundant cabinetry, and a wine fridge — ideal for hosting and extra prep space. A conveniently located full guest bathroom nearby provides privacy and easy access for visitors, separate from the primary and secondary bedrooms. Situated on beautiful Lake Ruby, the outdoor living is just as impressive along with beautiful sunsets. Spend evenings around the fire pit overlooking the water, relax in the screened-in patio, or host unforgettable gatherings in the spacious backyard. A dedicated grilling patio makes outdoor entertaining easy year-round and perfect for holidays, cookouts, and waterfront living at its finest.
Listing Agent: Anthony Dinova, Jr (407-800-9110)
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