Location: Maitland , 32751
Do Not Show Listings
2130 DELORAINE TRL, MAITLAND, FL 32751
$850,00011 Days on yellowkey MLS ID: O6397018
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2175 Built: 1964 Tax: $10,394 (2025)Community: Highland Park Estates First AddSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,394
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: Welcome to this beautifully renovated pool home in the highly sought-after Dommerich neighborhood of Maitland. Offering over 2,000 square feet of living space, this 3-bedroom, 2-bath residence perfectly blends modern upgrades with comfortable, functional living. Inside the home is designed for both everyday living and entertaining. The spacious living room serves as the heart of the home, featuring a stunning marble fireplace and seamless flow into multiple gathering areas, including a dedicated dining space just off the kitchen, a family room that leads to the outside and access to the bedrooms. The fully renovated chef’s kitchen is a true standout, showcasing soft-gray shaker cabinetry, quartz countertops, a Carrera marble backsplash, and stainless steel appliances. With ample counter space and a built-in water filtration system, this kitchen is as functional as it is beautiful. Throughout the home, you’ll find upgraded Italian wood-plank porcelain tile flooring, offering both durability and elegance. The primary suite provides a peaceful retreat with a walk-in closet and a fully updated ensuite bathroom featuring a double-sink vanity, granite countertops, and a spacious walk-in shower with marble and porcelain finishes. Step outside into your private backyard oasis. Designed for true Florida living, this space features a Pebble Tec pool, paver deck, covered gazebo with ceiling fan, a 65” outdoor TV, and a premium sound system perfect for entertaining or relaxing year-round. The lush landscaping, grassy area, and additional storage shed complete the outdoor experience. Additional highlights include a new roof (2019), A/C system (2021), WiFi-enabled irrigation system, fresh interior paint, and new LG washer, dryer, and dishwasher. Located in the desirable Dommerich area, just minutes from top-rated schools, dining, shopping, and major roadways, this home offers the perfect combination of location, upgrades, and lifestyle. This is the one you’ve been waiting for.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Mario Zendeli (407-325-3893)
67 CYPRESS LN, MAITLAND, FL 32751
$1,130,000100 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
Tax Year: 2024
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)
921 N THISTLE LN, MAITLAND, FL 32751
$1,100,0001 Day on yellowkey 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
Taxes:$4,489
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)
354 HICKORY DR, MAITLAND, FL 32751
$375,0004 Days on yellowkey MLS ID: O6398112
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1395 Built: 1972 Tax: $2,884 (2024)Community: Druid Hills ParkSingle Family
Taxes:$2,884
Elementary School: Lake Orienta Elementary
High School: Lyman High
Middle School: Milwee Middle
Remarks: Multiple offers received, asking for highest and best before Sunday, April 19th at 5pm! Welcome Home to 354 Hickory Drive — Where Your Next Chapter Begins! Nestled in the friendly Druid Hills community of Maitland, FL, this beautifully renovated 3-bedroom, 2-bathroom home is the perfect place to plant roots and make lasting memories. Whether you're buying your first home or looking for the ideal space to grow your family, this one was made for you. The open-concept floor plan makes everyday life easy and fun — from homework at the kitchen table to hosting friends and family on the weekends. The fully updated kitchen, renovated bathrooms, and new flooring throughout mean you can move right in and start living without the stress of costly upgrades. When it's time to unwind or play, the huge enclosed screen porch and deck deliver the outdoor lifestyle Florida is known for — shaded space to play or a relaxed spot to decompress after a long day. The .20-acre lot gives the whole family room to run, garden, or just enjoy the Florida sunshine. Big-ticket items are already taken care of, so you can focus on building your future rather than your repair list — featuring a 2025 AC, 2024 tankless water heater, 2023 water softener, whole house water filtration system, 2018 roof, and propane tank that feeds the water heater. For added convenience a stub out is readily available for future appliances. Located in the heart of Maitland with easy access to top-rated schools, family-friendly parks, local shopping and dining, major commuter routes — everything you need is right at your doorstep. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Jennifer Suarez (203-837-7830)
2801 WAUMPI TRL, MAITLAND, FL 32751
$864,90026 Days on yellowkey MLS ID: S5146322
REDUCED by $14,100 (1.6%) on 04/18/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2836 Built: 1972 Tax: $305 (2024)Community: Dommerich Hills 6Th AddSingle Family
Taxes:$305
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to Dommerich Hills! This fully renovated property delivers clean modern design with real functionality with NO HOA with a paver driveway, and double-door entry set the tone from the start. Inside, a bright open layout is anchored by a statement kitchen featuring sleek cabinetry, stainless steel appliances, and a waterfall island with custom wood detailing. The bathrooms follow with spa-inspired finishes, glass-enclosed showers, and modern fixtures throughout. Step outside to a covered lanai overlooking a private pool and expansive paver patio built for true Florida indoor outdoor living. Move in ready and designed to stand out, Located just minutes major highways, premium shopping, dining, and entertainment, this home delivers convenience and lifestyle all in one to the city beautiful. call to make a appointment to see this amazing Home.
Listing is courtesy of: AVANTI WAY REALTY LLC (305-229-1146)
Listing Agent: Javin Lopez (407-873-6606)
1230 HOLLYRIDGE TRL, MAITLAND, FL 32751
$574,90038 Days on yellowkey MLS ID: O6389346
REDUCED by $10,100 (1.7%) on 04/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1641 Built: 1983 Tax: $1,955 (2024)Community: Dommerich Woods Unit 2Single Family
Taxes:$1,955
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: South Seminole Middle
Remarks: Dommerich Woods gem! Tucked away on a cul-de-sac street in one of Maitland’s most sought-after neighborhoods, this beautifully updated 3-bedroom, 2-bath block home is the one you’ve been waiting for. Move-in ready and genuinely charming from the moment you walk in. The open floor plan feels airy and welcoming, with vaulted ceilings and natural light pouring through every room. The living room centers around a classic brick fireplace that anchors the space perfectly, while the kitchen is a true standout-quartz countertops, stainless appliances, 40-inch soft-close shaker cabinets and a built-in pantry. The layout flows effortlessly between living, dining and family spaces, making it as functional as it is inviting. The split bedroom layout offers great privacy for everyone. The primary suite is a real retreat- vaulted ceiling, spacious walk-in closet and a completely redone en-suite bath with a lovely garden window. Both bathrooms have been given a fresh, modern look that feels clean and polished. The updates list is long and impressive: newer LVP flooring throughout, AC (2022), water heater (2023), roof replaced in 2016, replumbed in 2008, newer paint inside and out, newer light fixtures and ceiling fans. Laundry is indoors and connects right to the two-car garage-a detail you’ll appreciate daily. Out back, the yard is a genuine sanctuary. Mature trees, lush landscaping and total privacy make it the kind of space you’ll actually use. A large shed with 50-amp power is ready for a workshop, hobby space or serious storage-and with no HOA, bring the toys too! Just minutes from Kewannee Park, the Seminole bike trail and easy access to major roads and local shops and restaurants. It’s a rare find in a neighborhood where homeowners rarely leave. Come take a look.
Listing is courtesy of: BOWERBIRD REALTY (407-716-0239)
Listing Agent: Stephanie Doucette (407-716-0239)
570 DOMMERICH DR, MAITLAND, FL 32751
$975,00051 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)
2600 MOHAWK TRL, MAITLAND, FL 32751
$669,00018 Days on yellowkey MLS ID: O6392479
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2265 Built: 1965 Tax: $3,038 (2025)Community: Dommerich Hills Second AddSingle Family
Taxes:$3,038
Remarks: Dommerich Hills – Maitland Positioned in the heart of Maitland, this inviting single-story home in the highly desirable Dommerich Hills community combines comfort, character, and location. Offered for the first time in 60 years, this property reflects true pride of ownership and long-term care. Set on a spacious .24-acre lot, the home offers 4 bedrooms, 2.5 baths, and 2,265 sq. ft. of living space. A timeless brick exterior and side-entry two-car garage create strong curb appeal, while the single-level floor plan provides effortless everyday living. The kitchen flows naturally into the connected living and dining areas, promoting an open, comfortable layout perfect for gatherings or flexible work-from-home use. Enjoy a fully fenced backyard great for pets, gardening, play, or weekend entertaining in your own outdoor retreat. Recent updates include: roof (Nov 2021), HVAC (May 2023), garage door (Apr 2022), and now connected to the city sewer (Nov 2025). Dommerich Hills is a well-established, tree-lined neighborhood known for its spacious lots, mid-century architecture, and strong sense of community. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High, with the convenience of walking or biking to nearby schools. Minutes from Downtown Winter Park dining, boutique shopping, and easy access to major roadways and everyday conveniences. A rare opportunity to own a meticulously maintained home in one of Maitland’s most established and sought-after communities—offering the perfect blend of location, lifestyle, and long-term value.
Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC (407-599-7070)
Listing Agent: Anthony Consalvo (407-599-7070)
410 POPLAR CT, MAITLAND, FL 32751
$345,00016 Days on yellowkey MLS ID: O6395891
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1254 Built: 1983Monthly Fee: $19 Tax: $4,731 (2025)Community: Branch TreeHalf Duplex
Taxes:$4,731
Remarks: Charming three bedroom, two bath home in the heart of Maitland! This thoughtfully updated home features an open layout with great natural light and an easy, flowing floor plan—perfect for everyday living and entertaining. The living spaces feel airy and inviting, with newly refinished wood flooring, vaulted ceilings and a split floor plan. Step outside to your fully fenced backyard, ideal for pets, play, or creating your own outdoor oasis. The screened-in covered porch is a total vibe—perfect for morning coffee, relaxing evenings, or hosting friends year-round Florida style. Big-ticket updates include a 2021 roof and 2021 AC, giving you peace of mind and added value. Whether you're a first-time buyer, downsizing, or looking for a smart investment, this home checks all the boxes with comfort, style, and location. Conveniently located near shopping, dining, and major roadways, you’ll love the accessibility and laid-back Maitland lifestyle.
Listing is courtesy of: PALMANO GROUP RE BROKERAGE LLC (321-214-1211)
Listing Agent: Heather Kolin (407-982-0305)
1400 LAKE SHADOW CIR #10103, MAITLAND, FL 32751
$155,0001 Day 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)
204 QUAYSIDE CIR #201, MAITLAND, FL 32751
$482,0001 Day on yellowkey 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)
51 OAKLEIGH LN, MAITLAND, FL 32751
$1,240,0003 Days on yellowkey MLS ID: O6399404
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4149 Built: 1972 Tax: $5,558 (2025)Community: Oakleigh Third AddSpa: NoSingle Family
Taxes:$5,558
Remarks: Come see 51 Oakleigh Ln, a functional residence arranged for everyday practicality. A comfortable living space features a fireplace. The kitchen includes an accent backsplash and all stainless steel appliances. The primary bedroom has a walk in closet, and its bathroom features double sinks and a separate tub and shower. Outside, a covered patio connects to an in ground pool within a fenced in backyard. This property is a must-see for comfort and outdoor living. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
106 OAKWOOD DR, MAITLAND, FL 32751
$649,90035 Days on yellowkey MLS ID: O6390412
REDUCED by $30,000 (4.4%) on 04/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1877 Built: 1963 Tax: $1,940 (2024)Community: N/ASingle Family
Taxes:$1,940
Remarks: One or more photo(s) has been virtually staged. MAJOR PRICE IMPROVEMENT Fully reimagined designer pool home with deeded access to skiable Lake Seminary, offering a rare blend of modern luxury, privacy, and prime Maitland location. Tucked away in a peaceful setting, this home lives like a private retreat while remaining just minutes from everything Maitland and Winter Park have to enjoy. At the heart of the home is a true showpiece kitchen, thoughtfully designed with a striking waterfall-edge island, full-height quartz backsplash, beverage fridge, and a clean, modern aesthetic reminiscent of a custom build. The open-concept layout is filled with natural light and flows effortlessly into the main living spaces—perfect for both elevated entertaining and everyday living. The primary suite delivers a spa-inspired retreat, featuring a freestanding soaking tub, oversized walk-in shower with dual heads, and carefully curated designer finishes that create a true sense of escape. Step outside to your own private backyard oasis, complete with a sparkling pool, expansive paver patio, and newly fenced yard—designed for both relaxation and hosting. The oversized lot offers exceptional flexibility, with ample space to add a garage, guest house, or additional storage to suit your needs. This home has been fully renovated with a strong emphasis on quality craftsmanship and high-end finishes throughout, including a new roof, HVAC, windows, flooring, and more—offering true move-in-ready peace of mind. Enjoy deeded access to skiable Lake Seminary via recorded easement—an exceptional and increasingly rare feature in this area. Buyer to verify access and use. Conveniently located near Maitland and Winter Park, with easy access to shopping, dining, and major roadways—giving you the perfect balance of privacy and accessibility.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Kikzeny Cartagena (215-359-6910)
1321 BENEVOLENT ST, MAITLAND, FL 32751
$374,90067 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
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
$825,00036 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
$599,00016 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)
1994 KENASTON RD #1994, MAITLAND, FL 32751
$415,00092 Days on yellowkey MLS ID: O6374243
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2103 Built: 1982 Tax: $4,582 (2025)Community: Ultra Vista CondoSpa: NoCondo
Taxes:$4,582
Remarks: Located in the desirable city of Maitland, just three miles from Winter Park’s renowned Park Avenue, this extensively updated 3-bedroom, 3.5-bath townhouse offers modern living in a prime Central Florida location. Tucked within a quiet residential setting and zoned for highly rated Seminole County schools, the home provides easy access to dining, shopping, and entertainment while maintaining a sense of privacy and comfort. The thoughtfully designed layout offers flexibility and convenience across two levels. The main floor features a spacious primary bedroom complete with a walk-in closet and private bathroom. Also on the first level is a welcoming living area with vaulted ceilings, creating an open and airy feel, along with a dining space that looks out through French doors. The kitchen is well-appointed with stainless steel appliances, stone countertops, and ample workspace, making it ideal for everyday living and entertaining. A screened rear porch extends the living space outdoors, perfect for relaxing or enjoying Florida evenings. Upstairs, you’ll find a second primary bedroom with an attached bathroom, offering a private retreat for guests or multi-generational living. A third bedroom, also with its own bathroom, is located just off a landing that overlooks the living area below, adding architectural interest and an open-concept feel. Significant updates completed in 2024 enhance both comfort and long-term value, including a new roof, upgraded air conditioning system with a 10-year manufacturer warranty, fully updated plumbing, and modern electrical improvements with new breaker boxes, switches, and receptacles. Interior finishes include wood flooring on the main level, luxury vinyl plank flooring upstairs, tile in wet areas, energy-efficient Low-E double-pane windows, recessed LED lighting throughout, and updated fixtures in the kitchen and closets. The exterior was freshly painted in 2025, adding to the home’s curb appeal and move-in-ready condition. With its low-maintenance design, versatile floor plan, and unbeatable location near Winter Park’s Park Avenue and the scenic Chain of Lakes, this home presents
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Veronica Figueroa (407-519-3980)
335 W LAKE FAITH DR #S, MAITLAND, FL 32751
$249,900191 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
$219,500176 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)
1140 S ORLANDO AVE #F-1, MAITLAND, FL 32751
$385,00064 Days on yellowkey MLS ID: O6381321
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 816 Built: 1969Monthly Fee: $546 Tax: $3,419 (2025)Community: Lake Maitland Terrace AptsCondo
Taxes:$3,419
Remarks: This condo was completely renovated in 2023 and is located in one of the best spots within the complex. Positioned directly on the Winter Park chain of lakes, it offers excellent access to everything Winter Park and Maitland have to offer. Residents enjoy being within walking distance to a variety of restaurants and shopping, creating an ideal blend of convenience and lifestyle. This unique corner unit features great views and a screened-in porch on the first floor, perfect for enjoying the surroundings. Because it is a corner residence, the condo is filled with lovely natural light from multiple windows, enhancing the open feel. Its location also provides easy access to the pool area for added everyday convenience. Inside, the condo offers two full baths and extensive upgrades throughout. Raised ceilings contribute to the spacious atmosphere, while newer electrical, plumbing, and a hot water heater provide peace of mind. The home includes newer full-sized appliances, custom cabinetry, granite countertops, newer flooring, custom closets, and an in-unit washer and dryer. Residents enjoy lake access with beautiful views and the community amenities include a clubhouse with a full kitchen, kayak racks, a fishing pier, and a personal storage unit. With renovations completed in 2023, the condo features modern finishes and systems that feel fresh and move-in ready.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Nick Mckee (407-913-0171)
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