Location: Maitland
Do Not Show Listings
775 WOODSIDE RD, MAITLAND, FL 32751
$449,00035 Days on yellowkey MLS ID: O6403039
0 Days Off yellowkey (back on 5/10/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1456 Built: 1973 Tax: $3,458 (2025)Community: Forest Brook 5Th SecSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,458
Elementary School: English Estates Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: South Seminole Middle
Remarks: Under contract-accepting backup offers. Welcome to 775 Woodside Road, ideally situated on a quiet cul-de-sac just minutes from Maitland and Winter Park’s most popular destinations. This beautifully updated three-bedroom, two-bath home offers an open floor plan filled with inviting living spaces and abundant natural light. Luxury vinyl flooring was installed throughout the home in 2023, while plantation shutters in the living room and bedrooms add both style and privacy. Sliding glass doors from the dining area and primary bedroom open to the spacious backyard, offering plenty of green space and room for a future pool. The kitchen is both functional and welcoming, featuring soft-close cabinetry, quartz countertops, stainless steel appliances, a designer backsplash, farmhouse sink, and a breakfast bar perfect for casual dining or entertaining. All three bedrooms offer generous closet space, complemented by two additional hallway linen closets. The spacious primary suite includes a walk-in closet and an updated bath with a large glass-enclosed shower and dual-sink vanity. The guest bath features a shower/tub combination and an updated vanity. Recent improvements provide peace of mind and include a newer water heater (2019), HVAC system (2020), roof (2021), and a partial re-pipe to reroute the main sewer line (2021).
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Wendy Williams Crumit (321-356-8590)
1928 SOUTH BLVD, MAITLAND, FL 32751
$479,90032 Days on yellowkey MLS ID: R4910950
1 Days Off yellowkey (back on 5/8/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1879 Built: 1969 Tax: $3,564 (2024)Community: NorthgateSingle Family
Taxes:$3,564
Tax Year: 2024
Remarks: Under contract-accepting backup offers. A rare Maitland find that combines a spacious 4-bedroom layout. Enjoy the freedom of a non-flood zone and no HOA fees or restrictions. The "Big Three" are already done: Roof (2022), HVAC (2023), and Water Heater (2024). Bonus: Original windows successfully passed all 4-point and wind mitigation inspections. Inside, a wide-open interior is flooded with natural light, featuring newly installed recessed lighting and a newer refrigerator (1 year old). Relax on the large screened-in porch overlooking a private, fully fenced backyard. Steps from Aldi and minutes from Trader Joe's and Whole Foods in Winter Park. Ideally situated near both the Winter Park Library and the Seminole Casselberry Library. Major updates, prime location, and zero HOA. Buy with total confidence: A pre-listing home inspection was completed last week, and the reports (4 Point and WM) are available at no cost! Schedule your private tour today! Note: Some interior photos feature previous owner-occupant staging to highlight design potential. Property is tenant-occupied until June 30th.
Listing is courtesy of: LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV (407-207-2220)
Listing Agent: Doori Sung (407-630-1638)
873 CRANES CT, MAITLAND, FL 32751
$1,249,90067 Days on yellowkey MLS ID: O6394418
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
High School: Edgewater High
Middle School: Maitland Middle
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)
106 OAKWOOD DR, MAITLAND, FL 32751
$649,00083 Days on yellowkey MLS ID: O6390412
1 Days Off yellowkey (back on 5/6/2026)
REDUCED by $900 (0.1%) on 05/02/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1877 Built: 1963 Tax: $1,940 (2024)Community: N/ASingle Family
Taxes:$1,940
Elementary School: Lake Orienta Elementary
High School: Lyman High
Middle School: Milwee Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. FINAL SUBMISSION WINDOW – SELLER HAS SET A FIRM DEADLINE TO SECURE CONTRACT. ALL PROPOSALS DUE MAY 11. FULLY RENOVATED Maitland home offered for a limited time only. Seller will review all submitted contracts, including those below list price, and is open to structuring terms that work - including potential closing cost assistance or rate buydown with acceptable terms. Contracts must be submitted by May 11. Seller will make a decision immediately thereafter. This property will be removed from the market if not sold by the deadline. 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)
1135 THUNDER TRL, MAITLAND, FL 32751
$850,00087 Days on yellowkey MLS ID: O6385581
0 Days Off yellowkey (back on 5/5/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2966 Built: 1967 Tax: $6,279 (2025)Community: Dommerich Hills Fifth AddSpa: NoSingle Family
Taxes:$6,279
Elementary School: Dommerich Elem
High School: Winter Park High
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to 1135 Thunder Trail, a beautifully updated pool home in Maitland, Florida, located in the highly desirable Dommerich Hills neighborhood. Situated on an oversized lot with no HOA, this property offers nearly 3,000 square feet of flexible living space, combining comfort, functionality, and the best of Florida outdoor living. Step inside to an open and inviting floor plan featuring a formal living room and dining area that flow seamlessly into a spacious family room, perfect for everyday living and entertaining. The heart of the home is the fully upgraded gourmet kitchen, complete with high-end appliances, double ovens, large cooktop, stone countertops, custom cabinetry, oversized refrigerator, and a massive center island designed for gathering. The family room is warm and stylish with a fireplace, custom feature wall, and a built-in wine bar with beverage coolers, bar sink, and coffee station. Large windows fill the home with natural light and provide views of the private backyard oasis. The first-floor primary suite offers a true retreat with dual walk-in closets, French doors leading to the pool, and a renovated ensuite bathroom featuring double vanities and a walk-in shower. Upstairs, you’ll find an expansive bonus room (26x17) with a half bath and built-in daybed, ideal as a media room, game room, home office, or guest suite, plus three additional bedrooms, a full bath with dual sinks, and custom built-ins throughout. Step outside to your private backyard paradise, featuring a sparkling in-ground pool, outdoor shower, fire pit area, multiple gazebo seating spaces, mature landscaping, and fruit trees. The fully fenced yard offers privacy and plenty of space for pets or play, while built-in gas lines make outdoor cooking effortless. Recent upgrades include: * New roof (2022) * New windows (2021) * New doors (2025) * HVAC (2019) * Fresh interior paint & updated landscaping Additional features include a two-car garage, large indoor laundry room with cabinetry, irrigation well, city sewer, and abundant storage throughout. Located just minutes from Maitland Social, Maitland City Centre, shopping, dining, and parks—and zoned for top-rated schools including Dommerich Elementary School, Maitland Middle School, and Winter Park High School—this home offers the perfect combination of location, lifestyle, and value. If you’ve been searching for a move-in ready pool home in Maitland with no HOA and top schools, this is the one.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Angela Worachek Pllc (503-381-1575)
448 STONEWOOD LN, MAITLAND, FL 32751
$624,990101 Days on yellowkey MLS ID: O6385060
INCREASED by $19,990 (3.3%) on 05/04/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3308 Built: 1980Monthly Fee: $33 Tax: $11,256 (2025)Community: StonewoodSpa: NoSingle Family
Taxes:$11,256
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom pool home offering the perfect blend of space, style, and location! From the moment you walk in, you’ll love the open layout and rich hardwood floors that create a warm and inviting atmosphere throughout. Designed for both everyday living and entertaining, this home features a dedicated office plus separate living, dining, and family rooms—giving everyone their own space while still feeling connected. The updated fireplace serves as a stunning focal point in the main living area, enhanced by natural light pouring in through the skylights. Recent upgrades provide added peace of mind and value, including a paver driveway and new gutters installed in 2019, full home re-pipe in 2021, air ducts sealed and new insulation added in 2021, a new pool pump and new AC compressor (one unit) in 2022, and new bedroom flooring in 2023.The kitchen is a true standout with 42” cabinetry, granite countertops, and newer stainless steel appliances, all overlooking the main living areas for seamless entertaining. A built-in wet bar adds the perfect touch for hosting gatherings and holiday celebrations. Retreat to the spacious primary suite and enjoy large closets throughout the home, providing ample storage for every lifestyle. Step outside to your private backyard oasis featuring a sparkling pool and expansive deck—ideal for relaxing weekends, outdoor dining, and Florida sunshine year-round. Located with easy access to Uptown Altamonte, I-4, 436, and Maitland Boulevard, this home places you just minutes from Lake Lily, Winter Park Village, Downtown Winter Park, and Cranes Roost—offering endless options for dining, shopping, parks, and entertainment. This home truly checks every box—space, updates, location, and a pool to top it all off! ????
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Dominick Florio (321-377-4045)
2642 BROOKSIDE CT, MAITLAND, FL 32751
$629,00036 Days on yellowkey MLS ID: O6403669
Bed: 5 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2360 Built: 1970 Tax: $5,909 (2025)Community: Forest Brook 3Rd SecSingle Family
Taxes:$5,909
Remarks: Indulge in the epitome of modern living with this fully renovated masterpiece! Boasting a thoughtfully designed split floor plan, 5 bedrooms, and 2 bathrooms, this home offers the perfect blend of space, style, and versatility. The heart of the home, the sleek kitchen, is a culinary haven equipped with stainless steel appliances, and ample counter space with upscale quartz countertops and storage. It's a canvas for your culinary creations. Whether you're a passionate collector or a lover of occasional indulgence, the built-in wine cooler transforms ordinary moments into extraordinary ones. Beyond elegant glass doors, unveil an expansive living room that is sure to captivate. Bathed in natural light, this grand space invites relaxation, entertainment, and cherished family moments. With 5 well-appointed bedrooms, there's ample space for everyone. The split floor plan ensures privacy and convenience for all members of the household. The master bedroom is a sanctuary of sophistication and comfort. With its spacious design and thoughtful layout, it provides an inviting escape from the world outside. The en-suite bathroom complements the master suite with its lavish features, double vanities, and a spa-like shower - experience the touch of rainfall from above and immerse yourself in the lap of luxury with the ceiling-mounted shower head. A dedicated bonus room adds an extra layer of versatility, it's ideal for a home office, playroom, or creative studio, the space adapts to your unique needs. Don't miss the chance to call this fully renovated gem your own. With its spacious layout, and modern finishes.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Giancarlo Chavez (312-869-1888)
987 BRIGHTWATER CIR, MAITLAND, FL 32751
$1,100,00042 Days on yellowkey MLS ID: O6401747
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3270 Built: 1996Monthly Fee: $395 Tax: $12,450 (2025)Community: Maitland ClubSpa: YesSingle Family
Taxes:$12,450
Remarks: Your dream home awaits. Welcome to this exquisitely Renovated 4/4 PLUS OFFICE PLUS BONUS ROOM POOL HOME. Located in the gorgeous guard gated enclave of Maitland Club. From the moment you enter, soaring ceilings and an elegant 3-way split floor plan create a sense of openness and refined comfort. At the heart of the home lies a beautiful updated kitchen, complete with a spacious center island, induction cooktop, and newer appliances - seamlessly flowing in to the sunlit breakfast nook and invitation family room, where a gas fireplace adds warmth and charm. All of these living spaces overlook a breathtaking outdoor retreat featuring a sparkling oversized swimming pool, perfect for both quiet relaxation and lively entertaining. Designed with versatility in mind this 3 way split plan has an upstairs bonus room with a full bath, - ideal as a playroom, home theater, exercise room or even a combination of spaces due to it's large size. Set on a generous one-third acre lot, the property offers ample room for outdoor enjoyment, from a potential playground to a thoughtfully designed lanai with dedicated areas for dining and lounging. Every corner of this home invites you to linger and enjoy. Ideally located near everything you love, this home offers easy access to premier grocery destinations, vibrant shopping and dining, major roadways, perfectly blending luxury with everyday convenience. Just minutes from Whole Foods, Trader Joe’s, Altamonte Mall, and the renowned shops and restaurants along Park Avenue in Winter Park, you’ll enjoy the best of Central Florida living right at your doorstep. Well-maintained home with A/C replaced in 2017. Interior upgrades completed in 2020, including a updated kitchen, newer appliances, new flooring, and three beautifully renovated bathrooms. No pool heater. Homes of this caliber do not last long.... come experience it for yourself.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Gale Milgrim (407-443-9832)
360 LAKE SEMINARY CIR, MAITLAND, FL 32751
$4,999,000197 Days on yellowkey MLS ID: O6362152
Bed: 5 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 6466 Built: 2026 Tax: $3,536 (2024)Community: FloridahavenSpa: YesSingle Family
Taxes:$3,536
Elementary School: None
High School: None
Middle School: None
Remarks: Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space, where sophisticated architecture and bespoke finishes harmonize with the tranquil beauty of the lake. A striking floating staircase framed by floor-to-ceiling glass offers a captivating first impression, while the grand entry reveals uninterrupted vistas of the pool terrace and shimmering water beyond. The chef’s kitchen, anchored by a remarkable 20-foot island, features premier appliances, exceptional storage and a concealed full-service scullery, creating an environment for hosting with grace and ease. The great room continues the home’s celebration of light and space with walls of glass that welcome breathtaking lake views at every turn. The primary suite is a serene retreat, showcasing a spa-inspired bath with floating vanities, a freestanding soaking tub, an expansive glass-enclosed shower and extravagant walk-in closets designed for the discerning owner. A secondary bedroom suite and oversized laundry enrich the main level, while an expansive lanai with an extraordinary summer kitchen invites effortless alfresco living, an experience only genuine lakefront living can provide. The second floor unfolds into a generous game room, complete with a wet bar and kitchenette. Three beautifully appointed bedroom suites, two scenic balconies, and a purpose-built home theater create an environment tailor-made for indulgence and entertainment. A new boathouse, soon to be constructed, further elevates the lakefront lifestyle. With three garages, a contemporary parking court, and meticulously executed architectural detail, this residence embodies modern luxury at its most refined. Lake Seminary, home to just 35 exclusive residences, offers coveted privacy while remaining moments from boutique shopping, celebrated dining and best of Winter Park. Immediate access to Interstate 4 and surrounding beltways ensures effortless connectivity throughout Central Florida.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Mel Bernstein (407-810-4726)
1033 HAMLET DR, MAITLAND, FL 32751
$350,000207 Days on yellowkey MLS ID: O6359229
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1146 Built: 1994Monthly Fee: $52 Tax: $474 (2024)Community: Hamlet At MaitlandSingle Family
Taxes:$474
Remarks: This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's world-renowned theme parks. This 1,146 square foot home features an open-concept floor plan. Primary suite includes a walk-in closet and a private suite bathroom, plus two additional bedrooms that provide flexibility for guests, family or a home office. 1 car garage with a large driveway that accommodates 2 more cars. The property's best feature is solar panels owned outright! With an average monthly bill of $35.00!!! Don't miss your chance to make it yours - schedule a private showing today!
Listing is courtesy of: BOX REAL ESTATE LLC (954-526-3900)
Listing Agent: Bennie Olivo (954-305-0844)
2112 CHIPPEWA TRL, MAITLAND, FL 32751
$965,00064 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 is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Laura Lane Heidrich (321-662-7491)
1511 E HORATIO AVE, MAITLAND, FL 32751
$719,00045 Days on yellowkey MLS ID: O6401235
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2676 Built: 1957 Tax: $6,013 (2025)Community: Minnehaha ShoresSingle Family
Taxes:$6,013
Remarks: Welcome to your dream home located in the heart of Maitland, FL. This stunning 4-bedroom, 3-bathroom residence is a perfect blend of modern comfort and timeless elegance. Lease Purchase available with a downpayment. Total Living Area 2760 Sq Ft. As you step inside, you'll be greeted by an inviting foyer that leads to a spacious open-concept living area, featuring high ceilings and abundant natural light. The gourmet kitchen boasts quartz countertops, new appliances, and ample cabinet space, ideal for culinary enthusiasts. The adjoining dining area is perfect for entertaining guests or enjoying family meals. The master suite is a true retreat with a walk-in closet and an en-suite bathroom featuring a luxurious soaking tub, dual vanities, and a separate shower. Three additional bedrooms provide plenty of space for family or guests, while the three full bathrooms ensure convenience and privacy for all. Outside, the large backyard offers a serene setting with a covered fenced-in yard, perfect for outdoor dining or relaxing in the Florida sunshine. The newly meticulously landscaped yard is designed for low maintenance, allowing you to enjoy the beautiful surroundings without the hassle. This property is located in a prime location, just minutes away from top-rated schools such as Maitland Middle School and Winter Park High School. Enjoy easy access to local landmarks and attractions including the Maitland Art Center, Lake Lily Park, and the Enzian Theater. For your shopping and dining needs, the Maitland City Centre and Winter Park Village are just a short drive away, offering a variety of upscale boutiques, restaurants, and entertainment options. Don't miss this incredible opportunity to own a piece of Maitland's finest real estate. Schedule your private tour today and experience the elegance and convenience of 1511 East Horatio Avenue. This home won't last long!
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Gustavo Vargas (407-854-2161)
1074 HAMLET DR, MAITLAND, FL 32751
$308,000310 Days on yellowkey MLS ID: O6331672
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1076 Built: 1994Monthly Fee: $52 Tax: $1,135 (2024)Community: Hamlet At MaitlandSingle Family
Taxes:$1,135
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, convenience, and an unbeatable location. From the moment you step inside, you’ll notice the inviting layout featuring a spacious living area filled with natural light and a functional kitchen equipped with newer stainless steel appliances—perfect for everyday living and entertaining alike. The home sits on a fully fenced lot with durable vinyl fencing, offering both privacy and a secure space for pets or play. Just beyond your backyard, enjoy direct access to a public playground—an ideal setup for families or anyone who loves being outdoors without losing the comfort of home. With a low HOA and a prime location, this home offers easy access to some of the area’s most exciting new developments and local favorites. You’ll be just minutes from the brand-new Lifetime Fitness currently under construction, the state-of-the-art HostDime data center, Winter Park Village, Whole Foods, and Amtrak. Plus, with quick access to I-4, commuting and weekend getaways are a breeze. Whether you’re a first-time buyer, downsizing, or looking for a solid investment in a growing area, this property offers the perfect blend of value, lifestyle, and location. Don’t miss your chance to make it yours!
551 RUFFEL ST, MAITLAND, FL 32751
$299,90065 Days on yellowkey MLS ID: S5146986
REDUCED by $5,099 (1.7%) on 04/20/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1162 Built: 1970 Tax: $396 (2025)Community: Clark Homes AcresSpa: NoSingle Family
Taxes:$396
Remarks: Situated at the end of a cul-de-sac in the Eatonville/Maitland area, this home offers a great opportunity for a first-time buyer or someone looking to downsize. According to the owner, the property was rehabilitated by the county in 2017, with updates that included the HVAC, plumbing, and electrical systems, and the roof was replaced approximately 10 years ago. Conveniently located near I-4 and Winter Park, this home is just minutes from local eateries, the library, and public transportation.
Listing is courtesy of: RESIDENTIAL MATCHMAKERS LLC (407-286-1698)
Listing Agent: Buffy Barrott (321-332-4503)
2801 WAUMPI TRL, MAITLAND, FL 32751
$864,90074 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
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)
101 MARINER WAY, MAITLAND, FL 32751
$769,00057 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)
570 MANOR RD, MAITLAND, FL 32751
$12,500,000414 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)
310 WHITE OAK CIR, MAITLAND, FL 32751
$849,000140 Days on yellowkey MLS ID: O6373919
1 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2995 Built: 1973Monthly Fee: $35 Tax: $7,779 (2025)Community: Maitland Grove Unit 1Single Family
Taxes:$7,779
Remarks: Under contract-accepting backup offers. Welcome home to one of the established Maitland neighborhoods in a pristine location close to everything, Maitland Groves. A lovely brick walkway invites you up to a charming entrance with a bricked front porch. A four- or five-bedroom, four-bath home features nearly 3,000 square feet with a generous flex space, checks all the boxes. The spaces have been opened with living spilling into dining and a bay window adding charm to an ideal gathering room to entertain in. Custom tile throughout for seamless design with an abundance of light making the spaces inviting and easy to relax in. Kitchen is updated with custom 42-inch wood cabinets, custom moldings, stainless appliances with new dishwasher, gas range and oven, granite counters with counter seating, and unbelievable storage and cabinet space. Florida room spans the back of the house with a bricked floor, a wet bar and a dedicated office/bedroom. Updated primary bedroom with a large walk-in closet. Main bath with dual sinks and new rainfall shower heads, tower storage cabinets, seamless glass with walk-in shower, stone floor and custom tile. Outside patio enjoys a paver deck with large Florida pool and plenty of green space with room to grow. Other updates include roof (2021), solar energy system so energy bills are low, recently painted in select areas, wood laminate floors in all bedrooms, renovated second and third baths, spacious indoor laundry and mudroom for organization, fenced yard, recessed lighting in living spaces, re-plumbed, plantation shutters, 2021 pool pump, pool converted to saltwater system and new garage door. If you need space, this has it. Terrific schools, close to Interstate 4, downtown Maitland which is home to Lake Lily with a weekly farmers market, independently owned Enzian Theatre, world-class restaurants and fantastic community parks home to many community events.
Listing Agent: Alison Mosley (407-304-6458)
103 WHITECAPS CIR, MAITLAND, FL 32751
$2,000,00081 Days on yellowkey MLS ID: O6382220
0 Days Off yellowkey (back on 3/16/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3695 Built: 2026 Tax: $3,439 (2024)Community: Hollieanna Shores 1St AddSpa: YesSingle Family
Taxes:$3,439
Remarks: Under contract-accepting backup offers. Under Construction. A striking blend of refined luxury and sleek contemporary architecture, this exceptional new construction residence is set to be completed in July 2026. Designed for effortless living and elevated entertaining, the home showcases 5 well-proportioned bedrooms, 4.5 designer bathrooms, and approximately 3,695 square feet of thoughtfully curated interiors. From the moment you enter, you’ll experience a bright, open layout that flows seamlessly from one space to the next. At the heart of the home is a culinary-inspired kitchen, complete with premium appliances, custom cabinetry, quartz surfaces, and a generous island that invites gathering and conversation. The living and dining areas are ideal for hosting, framed by expansive windows that capture views of the outdoor retreat. The private primary suite feels like a personal spa, featuring a serene bath with dual vanities, a freestanding soaking tub, a walk-in shower, and a spacious wardrobe closet. Each additional bedroom offers comfort, style, and ample storage—perfect for family, guests, or a dedicated office. Outside, the property transforms into an outdoor sanctuary with a shimmering pool, a covered lanai designed for year-round enjoyment, and a fully equipped summer kitchen ready for unforgettable weekends. A rare opportunity to own a remarkable residence where modern design meets everyday livability—a home you’ll never want to leave.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Christopher Christensen (407-312-8003)
101 WHITECAPS CIR, MAITLAND, FL 32751
$2,150,000115 Days on yellowkey MLS ID: O6375435
1 Days Off yellowkey (back on 2/16/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4004 Built: 2026 Tax: $3,987 (2024)Community: Hollieanna Shores 1St AddSpa: YesSingle Family
Taxes:$3,987
Remarks: Under contract-accepting backup offers. Under Construction. An elite expression of sophisticated design and elevated living, this remarkable residence offers a resort-style experience that stands apart in Maitland. This home is positioned on a sprawling corner lot and immediately captivates with a grand façade and undeniable curb appeal. From the moment you step inside, the experience is dramatic and refined. An impressive foyer sets the stage for the elegant interiors beyond, where high ceilings, natural light, and thoughtfully curated finishes create an atmosphere of sophistication and comfort. Designed for both effortless daily living and elevated entertaining, the open-concept layout flows beautifully from the expansive living room into the formal dining space, framed by a striking wall of oversized sliders that open up to the spacious backyard/pool area. The heart of the home is the show-stopping chef’s kitchen featuring stunning Chantilly quartz countertops, a full Thermador appliance suite, and an oversized walk-in pantry. The primary suite is designed to feel like a five-star retreat, featuring a spa-inspired bath offering a freestanding soaking tub, dual vanities, a glass-enclosed walk-in shower, and an expansive closet. Adding to the home’s rarity and versatility, the main level also features a true guest suite perfect for hosting in comfort, as well as a dedicated office. Outside, the backyard is the definition of resort-style living. The sparkling pool and spa anchor the space, surrounded by a generous covered lanai with a summer kitchen and abundant room for lounge seating and al fresco dining. And beyond the home itself, the lifestyle is exceptional. Residents of Hollieanna Shores enjoy access to a shared boat slip giving you access to the Winter Park Chain of Lakes, offering a level of exclusivity and lake-life convenience that takes this property to another level. All of this is just minutes from Maitland City Centre, beloved local parks, the iconic Enzian Theater, and the upscale dining, shopping, and charm of Park Avenue. This home redefines what luxury living looks like in Maitland, where location, design, and lifestyle come together in a home that feels truly unforgettable.
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.