Location: Maitland
Keyword(s): Maitland Middle
Keyword(s) Middle School: Maitland Middle
Do Not Show Listings
921 N THISTLE LN, MAITLAND, FL 32751
$1,100,000Listed 04/17/2026 12:16PM MLS ID: R4911080
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2300 Built: 1967 Tax: $4,489 (2025)Community: Highland Park EstatesSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,489
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: Central location, fully renovated, A-rated schools, a resort-style pool - this Dommerich home checks every box - and it is move-in ready, turnkey for your lifestyle. Situated in one of Central Florida’s most sought-after neighborhoods for over 60 years, Dommerich is known for its top-rated schools, tree-lined streets, parks, and unmatched convenience. This home sits right in the heart of it all. Originally built in 1967 and thoughtfully reimagined in a top-to-bottom renovation completed in 2019, the property blends classic charm with modern design and systems. Major updates include roof, HVAC, plumbing, electrical, windows, doors, insulation, appliances, kitchen, primary wing addition, natural gas connection, and a Rinnai tankless water heater. Inside, the open-concept living and dining spaces flow seamlessly to a designer pool and screened patio, creating an ideal indoor-outdoor lifestyle. The modern kitchen features extensive cabinetry with drawer-based storage, a coffee bar, and easy access to the garage and main living areas. A standout feature is the 2019-built primary suite addition, offering vaulted ceilings, a custom walk-in closet, en-suite bath, laundry, utility closet, and direct access to the pool area. The home also includes a second primary bedroom with its own en-suite bath that doubles as a pool bath, plus two additional bedrooms and a shared hall bath. The curb appeal is anchored by a mature, storybook-style shade tree, setting the tone for the character found throughout the property.
Listing is courtesy of: VISTA NATIONAL MANAGEMENT INC (407-252-5052)
Listing Agent: Garrett Mcginnis (321-278-9511)
204 QUAYSIDE CIR #201, MAITLAND, FL 32751
$482,000Listed 04/17/2026 9:53AM MLS ID: O6394791
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
Elementary School: Lake Sybelia Elem
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)
1321 BENEVOLENT ST, MAITLAND, FL 32751
$374,90066 Days on yellowkey MLS ID: O6377413
REDUCED by $9,100 (2.4%) on 04/17/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1751 Built: 2006Monthly Fee: $520 Tax: $2,204 (2024)Community: Enclave/Maitland A-FTownhouse
Taxes:$2,204
High School: Edgewater High
Tax Year: 2024
Remarks: $9K BELOW APPRAISAL + SELLER OFFERING INTEREST RATE BUY-DOWN with acceptable offer. /// Why settle for "standard" when you can own a designer-caliber home in Maitland with a lower monthly payment? Priced at $374,900—well below the recent $384K appraisal—this high-end unit offers instant equity. *LIFESTYLE & LOCATION /// RECLAIM YOUR TIME: Just 10 minutes to Downtown Orlando or Winter Park. PET FRIENDLY: Montecino is a gated, pet-loving community. LAKE CHARITY: Enjoy a scenic walk right outside your door. Maintenance-free living with a resort-style pool and gated security. *UPGRADES & VALUE /// MECHANICALLY NEW: New HVAC (Jan 2025), Bosch dishwasher, and 2026 fridge/microwave. DESIGNER FINISHES: Engineered hardwoods, fresh paint, and designer lighting. HOA BONUS: Monthly dues include High-Speed Internet, WiFi, and expanded TV/Streaming.*PEACE OF MIND /// Home just passed INSPECTION. Between the verified value, mechanical updates, and potential interest rate buy-down, this is the most secure and affordable luxury entry in Maitland.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Shirley Jones (407-719-9180)
1180 BANBURY TRL, MAITLAND, FL 32751
$825,00035 Days on yellowkey MLS ID: O6390521
0 Days Off yellowkey (back on 4/17/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2663 Built: 1968 Tax: $3,424 (2025)Community: Maitland Woods Third AddSpa: YesSingle Family
Taxes:$3,424
Remarks: This Maitland Woods charming home is located beneath the canopy of beautiful oak trees in one of Maitland’s most charming and established neighborhoods, this move-in ready pool home offers the perfect combination of space, updates, and location. Near the scenic shoreline of Lake Sybelia and quiet residential streets, the neighborhood feels peaceful and tucked away while still being incredibly convenient to everything Maitland has to offer. Just minutes away is the newly revitalized Downtown Maitland, where residents gather for outdoor movie nights, local restaurants, coffee shops, and ice cream on warm Florida evenings. The area shows a true small-town feel while remaining close to major roadways, SunRail, and downtown Orlando. Inside, the home offers a spacious and flexible layout designed for both everyday living and entertaining. A welcoming foyer opens to a large front living room and a dedicated office, perfect for working from home, a study, or creative space. The central dining room connects seamlessly to the kitchen and main living areas, creating an easy flow for gatherings and holidays. Toward the back of the home, an expansive family room serves as the heart of the house, offering plenty of space for relaxing while overlooking the backyard and pool. The bedrooms are thoughtfully positioned in a private wing of the home, including a generously sized primary suite with dual bathrooms and ample closet space. Two additional bedrooms share a nearby bath, and in addition to the three bedrooms the home also features the dedicated office, offering flexibility for guests, work, or hobbies. Step outside and enjoy Florida living year-round in this private backyard retreat featuring a resurfaced pool and spa, expansive patio, and covered lanai. The fully fenced yard and mature landscaping create both privacy and shade, making it an ideal setting for relaxing or entertaining. The home has been meticulously cared for with over $150,000 in improvements, including a kitchen remodel, bathroom renovations, updated HVAC system, newer roof with transferable warranty, updated pool equipment, new PEX plumbing, exterior paint refresh, irrigation inspection, and a new fence. Homes in this quiet Maitland neighborhood rarely become available, especially those that combine thoughtful updates, a spacious layout, and such close proximity to the charm, restaurants, and community events of Downtown Maitland and nearby Lake Sybelia.
Listing is courtesy of: LUXE HUNTER REAL ESTATE (407-984-4888)
Listing Agent: Allison Hunter (407-221-4669)
1161 CHARMING ST, MAITLAND, FL 32751
$599,00015 Days on yellowkey MLS ID: O6395711
REDUCED by $26,000 (4.2%) on 04/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2477 Built: 2006Monthly Fee: $520 Tax: $4,384 (2025)Community: Enclave/Maitland A-FTownhouse
Taxes:$4,384
Remarks: Sunrises over Lake Charity, two primary suites, and a kitchen made for serious cooking — this Montacino townhouse isn’t like anything else on the market. With 4 bedrooms, 3.5 baths, and new luxury vinyl flooring throughout, it’s effortlessly modern and move-in ready. The first-floor primary suite offers single-level living with a spa-inspired bathroom with two vanities, a tub and shower and generous closet space. The second-floor primary provides a private retreat for guests or family — a rare and highly sought-after layout. The brand new LG induction oven with air fryer and Café double dishwasher make cooking and cleaning a breeze, and the private back patio is perfect for morning coffee, entertaining or evening relaxation. An extra-large two-car garage adds plenty of storage for bikes, tools, or hobbies. Nestled in a gated community with a pool, this home blends comfort, security, and lifestyle convenience. With minutes to I-4, Winter Park, Downtown Orlando, and all of Maitland’s best dining and shopping are within easy reach. A rare floor plan, thoughtful updates, and flexible living spaces — this Montacino gem truly stands apart.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Allie George (407-457-4815)
335 W LAKE FAITH DR #S, MAITLAND, FL 32751
$249,900190 Days on yellowkey MLS ID: O6351302
REDUCED by $5,100 (2.0%) on 04/02/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1456 Built: 1974Monthly Fee: $571 Tax: $3,277 (2024)Community: Lake Faith Villas CondoCondo
Taxes:$3,277
Remarks: SELLER MOTIVATED. Welcome to Tranquility and Relaxation in this quiet meticulously maintained Gated Condominium Community- Lake Faith Villas. This beautiful community rests on the shores of Lake Faith in Maitland and is truly a Hidden Gem. This tastefully updated 2 bedroom 2.5 bath 2- Story END UNIT is nestled in a prime location within the community featuring an Updated Spacious Kitchen with beautiful Natural Shaker Style Cabinetry, Granite Counter Tops, Travertine Back Splash, Stainless Steel Appliances (Range/Oven 2025) and a beautiful eat in Kitchen Area overlooking the lush gardens. This townhome also features a Half Bath and Laundry Closet on the first floor along with an open Living Room Dining Room combination with first floor access to the back porch area with Double Sliders. There are two generously sized Bedrooms on the second floor featuring updated Vanities in the baths and plenty of natural light. This townhome also features a Covered Carport Parking Spot adjacent to the unit, an additional assigned parking spot AND a storage closet. Residents have access to an array of community amenities including a Clubhouse and an oversized pool overlooking the beautiful views of Lake Faith. This community is centrally located with easy access to the Maitland Exchange, I4 and 1792 and surrounded by an array of shops and restaurants. ****BRAND New AC Condenser installed 10/2025**** Community Improvements: All Roofs were replaced in 2021. All Building exteriors were repainted in 2025. Roads, Driveways and Lots re-milled and re-paved in 2025. Pool Restrooms were renovated in 2025. Clubhouse Restrooms are currently being renovated. Don’t miss your opportunity to live and enjoy this beautiful Villa Condominium Community.
Listing is courtesy of: GATE PROPERTIES & MANAGEMENT INC (407-704-7904)
Listing Agent: Nicholas Wild (407-704-7904)
1009 GROVE ST #1009, MAITLAND, FL 32751
$219,500175 Days on yellowkey MLS ID: O6353973
REDUCED by $5,500 (2.4%) on 04/03/2026
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1353 Built: 1972Monthly Fee: $483 Tax: $2,929 (2024)Community: Park Lake TownhousesCondo
Taxes:$2,929
Remarks: Incredible location! This beautifully updated 2 bedroom, 1.5 bath condo in Maitland is located minutes from shops, restaurants and offers easy access to I-4!. New windows! New electrical panels 2026, New water heater 2026. The stylish kitchen features granite countertops, 42 inch cabinetry, built-in wine glass rack, stainless appliances, pass thru window, and a long breakfast bar. Updated half bath downstairs for convenience. Both spacious bedrooms are located upstairs and share an updated bath with a glass enclosed tiled shower with rain shower fixtures. Laminate wood and tile flooring throughout! No carpet! Indoor laundry room with lots of storage with Maytag appliances. French doors lead you to a private fenced patio and one car garage! Step right outside the front door to the sparkling pool! Security system included. Zoned for sought-after schools, Dommerich Elementary, Maitland Middle, and Winter Park High. The neighborhood features a community pool, dock on Lake Gem and gorgeous landscaping and trees.
Listing Agent: Ingrid Livingston (407-595-5972)
790 S LAKE SYBELIA DR, MAITLAND, FL 32751
$975,00044 Days on yellowkey MLS ID: G5108209
REDUCED by $20,000 (2.0%) on 04/08/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2021 Built: 1958 Tax: $6,881 (2025)Community: Acreage & UnrecSingle Family
Taxes:$6,881
Remarks: One or more photo(s) has been virtually staged. Rare opportunity to own a private 0.66-acre Estate homesite in Maitland with deeded Lake Sybelia access. 790 S Lake Sybelia Drive offers a unique combination of land, privacy, and lake rights in one of Maitland’s most desirable communities. Set on a secluded, no-HOA .66 acre's of land, the property includes 12 feet of lake frontage extending approximately 268 feet into Lake Sybelia, providing true and usable access. Private lake access you can actually use — without the $2M price tag. The updated home features 3 bedrooms and 2.5 bathrooms, a warm living room with a wood-burning fireplace, a panoramic window seat, and a spacious Florida room. Move in and enjoy as-is, or take advantage of the property’s full potential. This property is ideal for expansion, a second-story addition, pool, guest house, or a custom new build, offering flexibility rarely found in Maitland. The 0.66-acre lot is fully fenced with mature landscaping and provides ample space for outdoor living, entertaining, storing your RV or Boat. Opportunities combining large land for privacy and Lake Sybelia access are increasingly rare. Recent updates include: Roof (2019), AC (2023), insulation (2025), and updated electrical and plumbing. Ideally located near Lake Sybelia Park, the Iconic Enzian Theater, Maitland Art & History Center, Lake Lily Park, and just minutes to Winter Park and Downtown Orlando. Enjoy paddleboarding at sunrise or relaxing in your private backyard retreat — this property delivers a rare blend of space, privacy, and lake access in the heart of Maitland.
Listing is courtesy of: LISA REALTY PARTNERS (407-500-5472)
Listing Agent: Lisa Pownall (407-927-1698)
2112 CHIPPEWA TRL, MAITLAND, FL 32751
$965,00015 Days on yellowkey MLS ID: O6394702
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2407 Built: 1961 Tax: $2,725 (2025)Community: Dommerich HillsSpa: NoSingle Family
Taxes:$2,725
Remarks: LONG AWAITED ARRIVAL IN DESIRABLE MAITLAND SUBDIVISION This beautiful, impeccably maintained and updated four bedroom three and a half bath pool home absolutely has it all! Perfectly located in Maitland’s much sought after Dommerich neighborhood and walking distance to top rated elementary and middle schools. This attractive split-floor plan offers four spacious bedrooms and three full baths on the first level and a bonus room/5th bedroom with half bath on the second level. The gorgeous kitchen boasts handsome, solid wood cabinets, granite countertops and stainless steel appliances with double ovens. The first floor open layout includes a large dining area with double fireplace leading into a wonderfully sized family room with fireplace and custom built-ins. Newly installed double pane, hurricane proof French doors brings in tons of natural light and leads out to your private oasis including newly resurfaced pool and brick paver deck, open patio and super fun gazebo with gas grill and nighttime lighting for entertaining! This home is fully supported by a full Generac system, never to be without power. Entire interior just freshly painted and new carpets installed in bedrooms and bonus room. Newer Roof (2021), HVAC (2020) and Tankless water heater. Samsung washer and dryer also included. Beautiful landscape and outdoor lighting add to its charm and warmth. THIS opportunity does not come along often. Look forward to meeting you there!
Listing Agent: Laura Lane Heidrich (321-662-7491)
570 DOMMERICH DR, MAITLAND, FL 32751
$975,00050 Days on yellowkey MLS ID: O6377363
REDUCED by $25,000 (2.5%) on 03/31/2026
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
Remarks: One or more photo(s) has been 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)
101 MARINER WAY, MAITLAND, FL 32751
$769,0008 Days on yellowkey MLS ID: O6396663
0 Days Off yellowkey (back on 4/16/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2413 Built: 1972Monthly Fee: $8 Tax: $3,528 (2025)Community: Maitland IsleSpa: NoSingle Family
Taxes:$3,528
Remarks: Under contract-accepting backup offers. Welcome to an exceptional residence in the Maitland Isle subdivision, where timeless elegance meets modern comfort. This beautifully updated four-bedroom, two-bath home spans 2,413 square feet and offers exclusive private lake access to Lake Maitland on the prestigious Winter Park Chain of Lakes. Designed for refined living and effortless entertaining, the home features a thoughtfully curated interior with upgraded finishes, including laminate flooring, enhanced baseboards, wet bar in family room and a seamless, light-filled layout. The kitchen, enhanced with quality wood cabinetry, flows seamlessly into the main living areas, while generously sized split bedroom plan provides flexibility for family, guests or a home office. A comprehensive list of upgrades reflects pride of ownership such as a newer roof (2020), resurfaced pool (2020), advanced air-conditioning system with Enviracare Elite air purification (2019), updated electrical panels (2012), replumbing (2006) and a water heater (2022). More recent enhancements include full interior and exterior painting (2025), a newly installed wooden fence and a serviced sprinkler system with a new impeller (2026). Outdoors, enjoy a private retreat with a sparkling pool and covered deck with an outdoor entertainment area, ideal for year-round Florida living. Residents of Maitland Isle benefit from exclusive access to Lake Maitland, offering a rare opportunity for boating and waterfront recreation within one of Central Florida’s desirable communities. Ideally in a top-rated school district and just a short distance to the charm of downtown Maitland, this home delivers a lifestyle of convenience, prestige and tranquility. A rare offering where location, quality and lifestyle converge.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Maryanne Branner (321-377-3909)
1420 LYNDALE BLVD, MAITLAND, FL 32751
$1,050,00018 Days on yellowkey MLS ID: O6394855
REDUCED by $50,000 (4.5%) on 04/16/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2470 Built: 1966 Tax: $12,772 (2025)Community: Maitland Park SouthSpa: NoSingle Family
Taxes:$12,772
Remarks: LOOK NO FURTHER! This completely remodeled POOL home boast a spacious 4 bedroom's and 2.5 bathroom's that are situated on an oversized corner lot (.26 acre). NEW plumbing, NEW fixtures, NEW kitchen, NEW bathrooms and more! From the moment you enter the front door, you can notice the large new tile floors, complimented by all custom cabinetry, high end light fixtures and a spacious floorplan. A gourmet kitchen with beautiful, light quartz counters to compliment the light and navy blue cabinetry. Retreat to the Master Suite with a stunning ensuite master bathroom featuring a glass enclosed shower with rain head, dual vanity and a modern garden tub great to soak away the stress from the day. Time to have some fun in the backyard! Jump right into the sparkling pool or lounge on the large open patio. The backyard is privacy fenced leaving a nice private space for entertaining and gathering with friends and family. This home is also in the perfect location just minutes from Park Avenue and many high end restaurants. Come check out you new home today!
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: Jason Zinno (407-467-5631)
2514 TUSCARORA TRL, MAITLAND, FL 32751
$759,00069 Days on yellowkey MLS ID: O6380728
REDUCED by $20,000 (2.6%) on 04/16/2026
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 3000 Built: 1971 Tax: $4,200 (2025)Community: Dommerich Hills 2 Nd AddSingle Family
Taxes:$4,200
Remarks: To Buyer “Discover the advantage of owning one of Tuscarora Trail’s premier homesites—where space, privacy, and lifestyle come together, all within the highly sought-after Dommerich school district, supporting both today’s living and tomorrow’s resale value. ” Nestled on a serene lakeside setting in the heart of Maitland, this beautifully upgraded 4-bedroom, 2.5-bath home offers more than just square footage—it delivers a lifestyle steeped in comfort, elegance, and Florida charm. Spanning nearly 3,000 square feet on a generous 0.43-acre lot, this residence frames breathtaking lake and sunset views that greet you with every evening breeze. Sunlight dances through expansive glass doors, illuminating open living spaces that flow effortlessly into a resort-style outdoor oasis complete with a sparkling private pool, covered patio, and lush water-framed views—perfect for quiet mornings with coffee or lively gatherings under starlit skies. Inside, thoughtful updates—like fresh interior and exterior paint, major systems enhanced for modern living, and paid-off solar panels for incredibly low utility costs—blend timeless Florida living with smart sustainability. Situated in the highly sought-after Dommerich Elementary and Winter Park school districts, this home embodies both tranquil retreat and everyday convenience. You’re just minutes from the charming boutiques, world-class dining, and cultural attractions of Winter Park’s Park Avenue, and a comfortable drive to Orlando’s theme parks—including Walt Disney World® Resort—and the region’s major airports for effortless travel. Whether you’re hosting family by the pool, savoring sunset reflections on the lake, or enjoying the top-tier schools and vibrant local lifestyle, 2514 Tuscarora Trail is more than a house—it’s home. NO HOA
Listing is courtesy of: NOELKE REALTY (407-607-7166)
Listing Agent: Tom Noelke (407-607-7166)
1140 S ORLANDO AVE #H-13, MAITLAND, FL 32751
$449,00042 Days on yellowkey MLS ID: O6387926
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 816 Built: 1964Monthly Fee: $546 Tax: $3,419 (2025)Community: Lake Maitland Terrace AptsCondo
Taxes:$3,419
Remarks: Experience turn-key living at its best in this beautifully renovated, designer-owned, lakefront condo, conveniently located in the sought-after Lake Maitland Terrace community on the Winter Park Chain of Lakes. This stunning 2-bedroom, 1-bath residence was thoughtfully redesigned with high-end finishes and an open, modern layout that maximizes both style and functionality. FURNITURE IS NEGOTIABLE! The completely updated interior features luxury “wood-like” vinyl plank flooring throughout, for enhanced durability. Enjoy a stylish kitchen with custom cabinetry, quartz countertops, tile backsplash, and newer appliances, and a beautifully remodeled bath with marble herringbone tile and designer fixtures. Additional upgrades include all new electrical, recessed lighting with dimmers, updated plumbing, custom closets, shiplap accents, new interior doors and trim, high-end Emtek door knobs throughout, and sound-reducing flooring underlayment for added comfort. Lake Maitland Terrace offers a true lakefront lifestyle, with private access to Lake Maitland, the largest lake on the Winter Park Chain. Residents enjoy a community dock and fishing pier, kayak & paddleboard racks, a sparkling pool, a clubhouse with lake views, shuffleboard courts, bike storage, and convenient on-site laundry....but this unit has it's OWN Washer and Dryer! Ideally located near shopping, dining, theaters, and just minutes from Park Avenue in Winter Park, this fresh and modern move-in ready condo offers effortless living in one of Maitland’s most desirable waterfront communities. Don't forget.... the FURNITURE IS NEGOTIABLE!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Marystuart Day (407-620-8683)
67 CYPRESS LN, MAITLAND, FL 32751
$1,130,00099 Days on yellowkey MLS ID: O6371328
REDUCED by $95,000 (7.8%) on 04/16/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2292 Built: 1979Monthly Fee: $8 Tax: $4,139 (2024)Community: Maitland ShoresSingle Family
Taxes:$4,139
Remarks: Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths. Step inside to discover hardwood floors flowing throughout the first level, leading to a dramatic sunken living room and formal dining room perfect for entertaining. The heart of the home is the spectacular family room featuring soaring 17-foot ceilings, a wood-burning fireplace, and expansive windows that bathe the space in natural light. The well-appointed kitchen boasts granite countertops, a charming breakfast nook, and glass sliders opening to a covered side porch—ideal for morning coffee or evening relaxation. The main level also includes a convenient guest bedroom and full bath, separate living and dining rooms, plus an attached 2-car garage. Upstairs, retreat to the loft-style primary suite with private en suite bath, two additional guest bedrooms, a hall bath, and laundry facilities for ultimate convenience. Outdoor living shines here with a front deck off the family room and multiple porch spaces. The quiet, dead-end street ensures peace and privacy. For just $100/year, the optional HOA provides deeded park access to beautiful Lake Maitland directly across the street—feel the refreshing lake breeze from your front door! Just minutes from the Winter Park Racquet Club and all that downtown Winter Park and Maitland have to offer. Zoned for award-winning Dommerich Elementary, Maitland Middle, and Winter Park High School. Complete with Terminix termite bond for peace of mind. This tranquil neighborhood retreat offers a rare combination of custom quality, natural beauty, and an unbeatable location. Don't miss this exceptional opportunity!
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
1393 BENEVOLENT ST, MAITLAND, FL 32751
$379,0001 Day on yellowkey MLS ID: O6399560
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)
105 TANGELO CT, MAITLAND, FL 32751
$1,798,999134 Days on yellowkey MLS ID: O6364116
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3203 Built: 2026 Tax: $6,909 (2024)Community: Hollieanna ShoresSpa: YesSingle Family
Taxes:$6,909
Remarks: Under Construction. A masterpiece of luxury design by LUIH Luxury Homes, perfectly positioned in the prestigious neighborhood of Hollieanna Shores. As you arrive, a striking façade with an elegant arched entryway sets an unforgettable tone. Beyond the front door, soaring ceilings and designer finishes frame an expansive living room where glass sliders dissolve the boundary between indoor and outdoor living, creating a seamless transition to the lanai and resort-style backyard. At the heart of the home, a chef’s kitchen designed for both performance and beauty exceeds every expectation. Sleek quartz countertops, a full Thermador appliance suite, custom cabinetry, and an oversized walk-in pantry elevate culinary experiences to a professional standard. The primary suite is a private sanctuary intentionally crafted to evoke a spa-like retreat. A stunning bathroom showcases a freestanding tub, an expansive walk-in shower, dual vanities, and exquisite finishes, while a large boutique-style closet with custom built-ins ensures every piece has its place. The upstairs level offers a generous loft and beautifully appointed secondary bedrooms, creating the ideal separation of space for family or guests. Outdoor living is nothing short of extraordinary, featuring a huge covered lanai with a full summer kitchen overlooking a shimmering pool and expansive, fully fenced backyard. Situated in the sought-after Hollieanna Shores neighborhood, this residence places you moments from Maitland City Centre, local parks, the iconic Enzian Theatre, and Park Ave. shopping and dining. If you’re seeking a home that feels both artful and effortless, this is where elevated living becomes reality.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Christopher Christensen (407-312-8003)
570 MANOR RD, MAITLAND, FL 32751
$12,500,000365 Days on yellowkey MLS ID: O6300040
Bed: 6 Bath: 8.5 Gar: 6 Liv Area Sq Ft: 11668 Built: 1996 Tax: $61,937 (2024)Community: Lake Maitland ManorSpa: YesSingle Family
Taxes:$61,937
Remarks: Welcome to Maison du Lac – a breathtaking lakefront estate that epitomizes unrivaled luxury, timeless elegance, and an extraordinary lifestyle. Situated on an expansive 2.7-acre lot along the prestigious Winter Park Chain of Lakes, this extraordinary residence showcases over 120 feet of pristine lakefront with sweeping panoramic views of the longest stretch of Lake Maitland. Blending classic Mediterranean architecture with state-of-the-art modern enhancements, Maison du Lac is a stunning fusion of enduring charm and contemporary sophistication. Originally constructed with timeless materials – including stucco exteriors and expansive windows – the home has been meticulously transformed into an 11,668-square-foot architectural masterpiece. Clean lines and open-concept living harmonize with rich textures and refined details, resulting in an environment that is both stately and smart. Upon entering through the grand 14-foot custom iron door, you are greeted by soaring dual staircases and exquisite finishes in marble, granite, and intricate moldings that reflect the home’s bespoke craftsmanship. A showstopping, $250,000 crystal chandelier—custom-designed and operable at the touch of a button—crowns the expansive great room, setting a dazzling tone for the professionally curated interiors. A private elevator adds convenience and accessibility across all levels of the home. The fully reimagined kitchen is a culinary showpiece, featuring top-of-the-line Wolf appliances, gleaming Cambria countertops, a large walk-in pantry, and expansive prep space ideal for entertaining at any scale. Whether hosting a lavish dinner or a relaxed brunch, the kitchen delivers both impeccable style and everyday functionality. The private master wing is an indulgent retreat, complete with a cozy fireplace, executive office, sauna, fitness room, and dual custom walk-in closets. Five additional en-suite bedrooms are thoughtfully positioned for maximum privacy, offering luxurious accommodations for family and guests. With seven full bathrooms and three half baths, the residence is ideally equipped for both refined daily living and grand-scale entertaining. For effortless indoor-outdoor living, multiple entertainment spaces flow seamlessly onto a sprawling lakefront patio. The outdoor summer kitchen, complete with a powered screen enclosure, provides the perfect setting for alfresco dining while enjoying sunset views over the water. A brand-new dock with a boat lift invites leisurely days spent boating, fishing, or simply relaxing on the lake. Outside, the estate continues to impress. Two serene fishponds with fountains create a tranquil sense of arrival, while the fully fenced and gated grounds ensure ultimate privacy. The residence is equipped with a full-home LUTRON smart system, offering intuitive control of lighting, ambiance, and automation. Additional features include a six-car garage, a resort-style swimming pool, newly updated landscaping, and custom exterior lighting. Maison du Lac is more than a home, it’s a lifestyle of distinction, privacy, and effortless sophistication. This is the lakefront living at its finest.
Listing is courtesy of: FORTUNE INTERNATIONAL REALTY (305-400-6393)
Listing Agent: Maggie Walas (407-701-0144)
223 QUAYSIDE CIR #C, MAITLAND, FL 32751
$575,000147 Days on yellowkey MLS ID: O6362370
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1734 Built: 1985Monthly Fee: $882 Tax: $4,185 (2024)Community: Moorings On Lake Maitland Condo Bldg 05Condo
Taxes:$4,185
Remarks: Welcome to refined living in The Moorings! This beautifully updated 3-bedroom, 2.5-bath townhouse offers 1,734 square feet of thoughtfully designed space in one of Maitland's most sought-after communities. The open layout showcases soaring ceilings and gleaming engineered wood floors throughout, creating an inviting atmosphere filled with natural light. The heart of the home is a stunning galley-style kitchen featuring crisp white cabinetry with glass-front doors, stainless steel appliances, and a cozy breakfast nook—perfect for morning coffee or casual dining. The living room centers around a charming wood-burning fireplace, while elegant French doors lead to a private screened patio overlooking serene common green space dotted with majestic oak trees. Upstairs, the primary suite serves as a tranquil retreat with a generous walk-in closet and spa-inspired en suite bath complete with a walk-in shower and double sink vanity. Two additional spacious bedrooms and a full bath complete the upper level, with ample storage throughout. Plantation shutters and updated light fixtures add polish to every room, while an attached one-car garage provides convenient parking and additional storage. Living in The Moorings means enjoying an exceptional lifestyle with exclusive access to a private community dock on Lake Maitland, a sparkling pool, and a welcoming clubhouse. The location is truly unbeatable—just moments from the charm of Lake Lily Park and its beloved weekly farmer's market, five minutes from the upscale boutiques and dining of Park Avenue, and surrounded by Central Florida's finest shopping, restaurants, and entertainment.
225 QUAYSIDE CIR, MAITLAND, FL 32751
$560,000197 Days on yellowkey MLS ID: O6338754
REDUCED by $35,000 (5.9%) on 04/03/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1734 Built: 1985 Tax: $3,080 (2024)Community: Moorings On Lake Maitland Condo Bldg 05Condo
Taxes:$3,080
Remarks: Discover the perfect blend of style and location in this beautifully updated 3-bedroom, 2.5-bathroom townhome in the sought-after Moorings community. With 1,734 square feet of thoughtfully designed living space, this residence offers a bright, open floor plan enhanced by vaulted ceilings and an abundance of natural light. The heart of the home is the stunning kitchen, showcasing white cabinetry, quartz countertops, stainless steel appliances, a decorative hood above the cooktop, and a classic subway tile backsplash. A charming bay window creates the perfect breakfast nook, while the open-concept living and dining areas provide ideal space for entertaining and everyday living. A wood-burning fireplace adds warmth and ambiance to the living room, creating a cozy focal point. Step through French doors into a sun-drenched sunroom with walls of windows overlooking tranquil community green space – your own private retreat for morning coffee or evening relaxation. Luxury vinyl plank flooring flows throughout the main level, complemented by plantation shutters and fresh paint. The second floor houses all three generously sized bedrooms, including a serene primary suite with a completely renovated en suite bathroom featuring a double sink vanity, walk-in shower, and spacious walk-in closet with custom built-ins. The updated hall bath offers a tub/shower combo and single-sink vanity. The second bedroom also features custom built-in closet organizers for added storage and convenience. Additional features include ceiling fans, interior laundry, and an attached one-car garage. Living in The Moorings means enjoying exclusive amenities, including a community dock on Lake Maitland, sparkling pool, and clubhouse. The location is unbeatable – just moments from Maitland's charming Lake Lily Park and its popular weekly farmer's market, five minutes from the upscale shops and dining of Park Avenue, and surrounded by the best of Central Florida's shopping, restaurants, and entertainment.
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