Refine Search
Map
Sort by
$215,000
2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code
A beautiful affordable condo in Maitland. 2 bedrooms and 1 ½ baths with a 1 car garage. The kitchen has been updated with white cabinets and new counter tops. The appliances have been updated. There is a large dining room and separate living room. The utility room is on the 1st floor with an updated barn door for access. The 1st floor has wood flooring while the second floor has carpeting. The second floor has two bedrooms with an updated bathroom. The shower has been remodeled to allow easy access. This home has a large patio with artificial grass flooring. The one car garage is an added bonus. The property has had the window replaced, a new water heater (2026) and the electrical panel upgraded within the past couple of years. The A/C system was replaced in 2022. This wonderful unit is at a great price and will not last long.

814 Park Lake Circle Unit 8, Maitland
$469,450
4 Beds ⋅ 2 Baths ⋅ Northgate SubDv. ⋅ 32751 Zip Code
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.

1928 South Boulevard, Maitland
$424,000
3 Beds ⋅ 2 Baths ⋅ Forest Brook 5th Sec SubDv. ⋅ 32751 Zip Code
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).

775 Woodside Road, Maitland
$495,000
4 Beds ⋅ 2 Baths ⋅ Forest Brook 3rd Sec SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Seller Motivated. Location, Location, Welcome to your new 4 BED 2 BATH home tucked away on a quiet cul-de-sac street in the desirable Maitland community of "Forest Brook" This one-of-a-kind home offers the perfect blend of charm, space, and functionality. Lovingly maintained, the home welcomes you with a grand Foyer, Formal Living and Dinng rooms, open family room, ideal for gatherings. A new updated Chef's Kitchen, complete with a gas range, beautiful Cherry cabinets, new appliances, and new Quartz countertops. The spacious Florida Room has a fun step up bar with pass through access to the kitchen. Perfect for entertaining and offers its own AC/Heater unit. Step outside to the large wrap around Deck. Tons of space for outdoor entertaining. No neighbors behind you, just tons of conservation space. Additional upgrades include Roof-2021, AC-2023-Fl Room, AC-2025, Gas Water Heater-2010, Kitchen appliances 2023, Electrical panel- 2024. This home is ideally located just minutes from Winter Park, Casselberry, Winter Springs, Easy access to shopping, dining, and major commuter routes. Start living your Best Life.

653 Green Meadow Avenue, Maitland
$520,000
3 Beds ⋅ 2 Baths ⋅ Greenwood Acres SubDv. ⋅ 32751 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to this beautifully updated 3 bedroom, 2 bathroom home offering nearly 1,600 square feet of comfortable living space in the heart of Maitland. Featuring a modern look throughout, this well maintained property showcases luxury vinyl flooring that flows seamlessly through the main living areas, creating both style and durability. The spacious layout includes generous living and dining areas, perfect for relaxing or entertaining, along with a functional kitchen that offers ample storage and workspace. A brand new roof installed in 2025 adds peace of mind and long term value. Step outside to enjoy a fully fenced backyard, ideal for privacy, pets, or outdoor gatherings. A wooden deck provides the perfect space for weekend barbecues or quiet evenings at home. Situated in a quiet, established neighborhood, this home offers a highly convenient location. You are just minutes from major roadways including I-4 and Maitland Boulevard, making commuting throughout Central Florida simple. Nearby shopping and dining options include Maitland Center, Altamonte Mall, and a variety of local plazas along Orlando Avenue. Parks, schools, and everyday essentials are all within easy reach, adding to the home’s overall appeal. This property combines modern updates, functional outdoor space, and a prime location, making it an excellent opportunity for a wide range of buyers.

636 Hillcrest Avenue, Maitland
$629,000
5 Beds ⋅ 2 Baths ⋅ Forest Brook 3rd Sec SubDv. ⋅ 32751 Zip Code
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.

2642 Brookside Court, Maitland
$232,000
2 Beds ⋅ 2 Baths ⋅ Lake Faith Villas Condo SubDv. ⋅ 32751 Zip Code
Enjoy easy living in this first-floor condo in the heart of Maitland. This well-designed unit offers a functional layout with natural light and a seamless flow between the kitchen and living space. Ground-floor access and a private patio make everyday living convenient and low maintenance. The bedroom is generously sized, providing a comfortable retreat. Ideally located just minutes from shopping, dining, major roadways, and Orlando. Perfect for a first-time buyer, someone who wants to downsize, or investor looking for strong potential in a prime area.

351 W Lake Faith Drive Unit 117, Maitland
$420,000
3 Beds ⋅ 3 Baths ⋅ Moorings On Lake Maitland Condo Bldg 04 SubDv. ⋅ 32751 Zip Code
Welcome to The Moorings on Lake Maitland, one of the most in-demand communities in the area. Consider this unit, 3-bedrooms and 2-1/2 baths, approximately 1700 square feet of living space with a 1-car garage, and overlooking the beautiful peaceful courtyard, to be your blank slate. Gleaming wood floors and fresh painted throughout, it is just waiting for you to make it your own. You'll love this comfortable living space, and there is so much to work with! From the entry foyer you'll find the eat-in kitchen immediately on your right. Head through the kitchen to the spacious dining room, and into the living room with vaulted ceiling and zen garden view. Half-bath and inviting screened lanai complete the ground floor living space. Upstairs you'll find the large primary suite, also overlooking the courtyard, and two more bedrooms, both front-facing, and a full bath in the hallway. The laundry room with washer, dryer and utility sink is in the garage. The grounds, pool and club house are maintained by the community, so all you have to so is enjoy the ambiance of the beautiful grounds and the lakefront. The many advantages to this convenient location include being on Lake Maitland, and, easy access to necessities like grocery and drug stores, and restaurants within walking distance. This one is priced to sell, so don't miss this opportunity!

245 Quayside Circle, Maitland
$800,000
4 Beds ⋅ 2 Baths ⋅ Maitland Woods SubDv. ⋅ 32751 Zip Code
Towering oaks and Spanish moss flowing in the breeze set the stage for this oasis in the heart of Maitland. This charming 4 bedroom, 2 bath abode with a tropical courtyard pool has been lovingly updated with luxe finishes and features. Step inside the covered airy breezeway where travertine pavers surround the screen enclosed pool deck and the true front door entrance. Beautiful crown moulding and wood-look ceramic tile flooring runs throughout the house (no carpeting). Double pane windows and sliders with build-in blinds accent the courtyard views. Arched doorways open to the poolside family room with wood-burning marble-surround fireplace and custom built-ins. Large enough for all your family and friends, the spacious living and dining rooms with custom window shutters and recessed lighting is sure to impress. Total kitchen remodel features handmade subway tile backsplash, quartz countertops, stainless steel appliances, and the most charming in-kitchen dining area with views out to the pool. A renovated full hall bathroom with double sink quartz vanity and tub/shower combo opens to the pool and is close to the 3 guest bedrooms (one bedroom also has sliders to the pool). Your large primary suite is tucked away at the back of the house with dressing area, walk-in closet, and separate toilet/shower room. And the views to the pool through the double sliders are inspiring. Indoor/outdoor living is a breeze in this unique Maitland courtyard style pool home. Plus, a fully fenced backyard is still big enough for children and pets to play. You’ll love the location with easy access to I-4, the shops and restaurants of Downtown Maitland and Lake Lily (home of a weekly farmer’s market), and walking distance to Lake Sybelia and lakefront Homer Hough Park. Improvements include NEW hot water heater 2026; NEW solar pool heater 2022; NEW paver driveway and motor court 2022; NEW roof 2021; NEW travertine pool deck 2021; NEW HVAC 2020; NEW Gernerac house generator; and Replumb CPVC 2015.

1170 Willowbrook Trail, Maitland
$90,000
Lakewood Shores SubDv. ⋅ 32751 Zip Code
Build your dream home on this perfect, residential vacant CORNER LOT in Maitland! NO HOA! Ideally located near top-rated schools, shopping, dining, parks, & major roadways! Come view it TODAY!

Lakewood Circle, Maitland
$498,000
3 Beds ⋅ 2 Baths ⋅ Forest Brook 3rd Sec SubDv. ⋅ 32751 Zip Code
Welcome to a home that doesn’t just check boxes — it supports your lifestyle. Tucked into one of Maitland’s beloved neighborhoods, Forest Brook, this delightful property blends comfort, practicality, and a little everyday serenity. *Lots of new since 2023: Whole house generator, 20’x12’ shed, front and back sod (just completed 4/2026), renovated driveway, gutters, vinyl fence in backyard & so much more!!* Home oozes charm showcasing a sunny yellow exterior with shutter details, white columns on covered front porch, fresh Florida style landscaping, finished concrete driveway, all leading you to covered front entry with pretty leaded glass front door. Step inside to tiled foyer entry and you’ll find a split floor plan offering privacy, flow, and room to spread out — whether you’re hosting, working from home, or simply enjoying a quiet morning. Separate formal dining room complete with sparkling chandelier and French door to patio has yard views. Generous living room has wood floors, new ceiling fan and wall of windows with double French doors to patio plus Plantation shutters. Inviting kitchen is a true gathering spot with a large island with seating on both sides, not to mention all the counter space, white cabinetry, complete stainless steel appliance package and new window above sink. Dedicated office/bonus space has ceiling fan and French door to patio with Plantation shutters. Spacious primary suite flaunts Plantation shutters, new ceiling fan, a walk-in closet plus an en-suite bath with adult height dual vanities, private commode and tiled shower stall. Two guest bedrooms on the other side of the home share updated bath with stylish modern vanity, dual sinks, decorative framed mirrors, chic light and a tub/shower combo. Unwind out back on the oversized covered and screened patio with dual ceiling fans offering lots of gathering space. Every room on the backside of the home contains a French door making it the perfect opportunity for that indoor-outdoor feel. Oversized backyard is fully fenced, freshly sodded and creates the perfect lush, green space ready for play, pets, gardening or gatherings. 20’x12’ shed is a dream for storage lovers or anyone who needs extra space – double doors, tons of room and endless possibilities. No power outages here! A whole house generator keeps life running smoothly no matter the weather. No scrambling, no stress — just uninterrupted comfort and security. Tree lined streets and quick access to parks, major connectors like 436, 414, N Orlando Avenue, Howell Branch Rd/Horatio, Red Bug Rd plus the YMCA, Advent Health and endless dining and shopping options like the Maitland City Center, Downtown Winter Park and so much more— it’s the kind of place where life feels a little easier and a lot more enjoyable!

612 Green Meadow Avenue, Maitland
$190,000
2 Beds ⋅ 2 Baths ⋅ Visconti West SubDv. ⋅ 32751 Zip Code
Virtually Staged. Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in the sought-after Visconti community, where comfort, convenience, and lifestyle come together. Located on the third floor, this light-filled residence features soaring vaulted ceilings that create an open, airy feel, complemented by abundant natural light throughout. Ideally positioned just steps from the clubhouse, you’ll enjoy effortless access to resort-style amenities, including a sparkling pool and fully equipped fitness center—perfect for both relaxation and an active lifestyle. This move-in ready condo is an excellent opportunity for both homeowners and investors alike. With quick access to I-4, commuting to Downtown Orlando is easy, while the shopping, dining, and entertainment of Altamonte Springs are just minutes away. Opportunities like this in Visconti don’t last—schedule your private showing today.

1100 Lake Shadow Circle Unit 2307, Maitland
$718,000
4 Beds ⋅ 3 Baths ⋅ Minnehaha Shores SubDv. ⋅ 32751 Zip Code
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!

1511 E Horatio Avenue, Maitland
$973,600
4 Beds ⋅ 3 Baths ⋅ Highland Park Estates SubDv. ⋅ 32751 Zip Code
Fully renovated pool home in the heart of Dommerich featuring a rare dual-primary layout and a 2019-built owner’s suite addition—designed for modern living and effortless maintenance. Originally built in 1967 and completely reimagined in 2019, the home blends timeless character with major system upgrades including roof, HVAC, plumbing, electrical, windows, and doors—providing peace of mind rarely found in this area. The home is vacant and move-in ready. The open-concept living and dining areas flow seamlessly into a private, resort-style backyard featuring a screened-in pool, covered patio, and low-maintenance landscaping. With xeriscaped grounds, paver walkways, and perimeter planting beds, the outdoor space is designed to be enjoyed—not managed. The kitchen is built for both function and flow, offering extensive drawer-based cabinetry, a dedicated coffee bar, natural gas cooking, and direct access to the main living areas and garage. The home is equipped with natural gas, supporting the cooktop, dryer, tankless water heater, and pool/spa heater—providing enhanced efficiency, faster performance, and lower operating costs compared to all-electric homes. The 2019-built primary suite is a true retreat with vaulted ceilings, pool access, a custom walk-in closet, en-suite bath, and a dedicated laundry space. A second primary bedroom with en-suite bath also serves as a pool bath—ideal for guests, multigenerational living, or flexible use. Two additional bedrooms and a shared hall bath complete the layout. Located in one of Central Florida’s most established and sought-after neighborhoods, Dommerich offers top-rated schools, tree-lined streets, parks, and unmatched proximity to shopping, dining, and major roadways. Vacant and move-in ready. Homes with this layout and level of renovation in Dommerich rarely come available. And the price was recently repositioned to provide one of the best values among fully renovated pool homes in Dommerich.

921 N Thistle Lane, Maitland
$155,000
1 Beds ⋅ 1 Baths ⋅ Visconti West Condo SubDv. ⋅ 32751 Zip Code
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!

1400 Lake Shadow Circle Unit 10103, Maitland
$467,000
2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code
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.

204 Quayside Circle Unit 201, Maitland
$735,000
5 Beds ⋅ 3 Baths ⋅ Dommerich Hills 6th Add SubDv. ⋅ 32751 Zip Code
Completely Remodeled 2026 | Single-Story | Split Floorplan | The redesigned kitchen features 42" shaker cabinetry, Calcutta quartz countertops, a marble backsplash, and new stainless steel Fisher & Paykel appliances. Bathrooms have been completely remodeled with updated finishes. Luxury vinyl flooring extends through all common areas, complemented by LED recessed lighting and updated fixtures throughout. The open layout provides clear sight-lines between the kitchen and family room, creating a connected main living area. The pavers meet manicured lawns and fresh landscaping for a clean, contemporary finish that is 100% move-in ready. Additional features include an interior laundry room and a fully fenced backyard with a pool. Enjoy being just minutes from Park Avenue, Lake Lily, and Maitland City Centre where you'll find farmers markets, local dining, and boutique shopping. With easy access to I-4, 417, and the Maitland Exchange, you're well connected to everything Central Florida has to offer.

2809 Waumpi Trail, Maitland
$1,100,000
5 Beds ⋅ 3 Baths ⋅ Kings Row SubDv. ⋅ 32751 Zip Code
1665 King Arthur Circle

1665 King Arthur Circle, Maitland
$1,075,000
4 Beds ⋅ 4 Baths ⋅ Oakleigh Third Add SubDv. ⋅ 32751 Zip Code
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 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

51 Oakleigh Lane, Maitland
$401,000
3 Beds ⋅ 2 Baths ⋅ Druid Hills Park SubDv. ⋅ 32751 Zip Code
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!

354 Hickory Drive, Maitland
$398,000
3 Beds ⋅ 2 Baths ⋅ Druid Hills Park SubDv. ⋅ 32751 Zip Code
STUNNING MODERN REVIVAL IN THE HEART OF MAITLAND. Welcome to 344 Banyan Drive, where classic Maitland charm meets contemporary elegance. Experience the pinnacle of move-in-ready luxury at 344 Banyan Dr. This impeccably renovated residence has been transformed from top to bottom with sophisticated finishes and meticulous attention to detail. The open-concept interior shines with all-new flooring, contemporary baseboards, and a fresh, designer paint palette. The newly renovated kitchen is a true showstopper, boasting new custom cabinetry, sleek stone countertops, a stylish tile backsplash, and a premium stainless steel appliance package. Both the living spaces and the fully renovated bathrooms feature all-new designer lighting that creates a warm, inviting ambiance throughout. Every inch of this home feels brand new. Don't miss your chance to own a masterpiece in 32751!

344 Banyan Drive, Maitland
$595,000
4 Beds ⋅ 2 Baths ⋅ English Woods SubDv. ⋅ 32751 Zip Code
Welcome to 2466 Fieldingwood Rd, a fully re-imagined pool home in Maitland, FL. This 4 bedroom, 2 bathroom home has been completely renovated from top to bottom with a fresh, modern feel that is move-in ready and designed for today’s lifestyle. From the moment you arrive, you will notice the clean exterior, updated landscaping, and quiet street that sets the tone for the rest of the home. ALL major systems have been updates: Roof 2022, Plumbing 2024, Hot Water Heater 2024, AC 2016, and newer pool equiptment. Inside, the layout flows effortlessly with light-filled living spaces, updated flooring, and a bright, open feel throughout. The kitchen and main living areas connect seamlessly, making it perfect for both everyday living and entertaining. Step outside to your private backyard retreat featuring a newly refreshed pool and spacious deck area. This is the kind of space that feels like Florida living should. Whether you are hosting friends or enjoying a quiet evening at home, this backyard delivers. The bedrooms offer comfortable, flexible space for families, guests, or a home office, while the primary suite provides a clean and calming place to unwind. Located in English Estates, you are just minutes from Winter Park with easy access to 17-92, 436, and Red Bug Lake Road. Commuting is simple with quick access to I-4 and the express lane entrance, getting you to downtown Orlando efficiently. If you are looking for a fully updated home with a pool in a central location that actually makes your day-to-day life easier, this is one you need to see in person.

2466 Fieldingwood Road, Maitland
$779,000
3 Beds ⋅ 2 Baths ⋅ Highland Park Estates First Add SubDv. ⋅ 32751 Zip Code
HUGE PRICE REDUCTION. 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.

2130 Deloraine Trail, Maitland
$330,000
3 Beds ⋅ 2 Baths ⋅ Druid Hills Park SubDv. ⋅ 32751 Zip Code
Virtually Staged. Welcome to 361 Hickory Drive, a truly special opportunity in a quiet, well-established community in the heart of Maitland. This charming home offers the perfect blend of comfort, mid-century historic charm and an unbeatable location making it ideal for those seeking both tranquility and convenience. Set on an oversized lot, this property provides ample space to entertain or enjoy the peaceful surroundings. The neighborhood is known for its quiet atmosphere with NO HOA, giving you the freedom to truly make this home your own without added restrictions. Upon walking in, you are greeted with an open concept living room space with the dining room to the left. The kitchen features ample cabinet space and a separate cooktop. The 2nd and 3rd bedrooms are generously sized with the primary including an en-suite bathroom. A BRAND NEW ROOF will be installed prior to closing, offering peace of mind. Upgrades include a New Water Heater (2026) and A/C(2019) ensuring comfort and efficiency. This home is also zoned in Top Rated Seminole County School Districts. Whether you're looking to settle into a serene neighborhood or invest in a property with strong fundamentals, this one checks all the boxes. Don’t miss your chance to call this Maitland gem home today!

361 Hickory Drive, Maitland
$899,000
4 Beds ⋅ 4 Baths ⋅ Dommerich Hills SubDv. ⋅ 32751 Zip Code
NEW PRICE…NEW OPPORTUNITY!! This beautiful, impeccably maintained and updated four bedroom and three and a half bath pool home absolutely has it all, including the added benefit of new electrical wiring throughout. 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 for 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 brick 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 the newly resurfaced pool with new pool pump and filter, brick paver deck, open patio, and super fun gazebo with gas grill and nighttime lighting for entertaining! Awesome potential to install gas into the kitchen, as well. This home is fully supported by a new 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. Gorgeous architectural landscape with LED lighting add to its charm and warmth. This opportunity does not come along often and is absolutely MOVE-IN READY! Look forward to meeting you there!

2112 Chippewa Trail, Maitland
$258,500
3 Beds ⋅ 2 Baths ⋅ Clark Homes Acres SubDv. ⋅ 32751 Zip Code
Under contract-accepting backup offers. 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.

551 Ruffel Street, Maitland
$650,000
4 Beds ⋅ 3 Baths ⋅ Dommerich Hills Second Add SubDv. ⋅ 32751 Zip Code
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.

2600 Mohawk Trail, Maitland
$578,000
3 Beds ⋅ 4 Baths ⋅ Oakland Shores SubDv. ⋅ 32751 Zip Code
Virtually Staged. Welcome to 502 Oak Lane in Maitland, a beautifully updated 3 bedroom, 3.5 bathroom pool home offering comfort, character, and peace of mind. Thoughtfully improved throughout, the home features fully updated plumbing, including the replacement of the original cast iron plumbing, along with a brand-new pool pump. Inside, you will find a well-designed layout with spacious living areas, updated finishes, and abundant natural light. Each bedroom has access to its own private bathroom, providing excellent privacy and flexibility for family members, overnight guests, or a home office. The home has been meticulously maintained and is truly move-in ready. Step outside to your private backyard oasis, complete with a swimming pool that is perfect for relaxing, entertaining, or enjoying Florida living year-round. Located on a quiet street in Maitland, the home is approximately 10 minutes from Winter Park and offers convenient access to major highways, shopping, dining, and everyday conveniences. This is a rare opportunity to own a fully updated pool home in one of Maitland’s most desirable and centrally located areas.

502 Oak Lane, Maitland
$824,900
5 Beds ⋅ 3 Baths ⋅ Dommerich Hills 6th Add SubDv. ⋅ 32751 Zip Code
Welcome to Dommerich Hills, where modern style meets everyday comfort. This beautifully renovated home offers the freedom of **NO HOA** and has been thoughtfully updated from top to bottom. From the paver driveway and elegant double-door entry to the bright, open-concept interior, every detail has been designed to make you feel at home. The heart of the home is a stunning chef-inspired kitchen featuring sleek custom cabinetry, stainless steel appliances, and a striking waterfall island with custom wood accents,perfect for entertaining family and friends. The spa like bathrooms has glass-enclosed showers, contemporary fixtures, and designer finishes that create a relaxing retreat. Step outside and discover your own private Florida oasis. A covered lanai overlooks the sparkling pool and expansive paver patio, creating the ideal space for outdoor dining, weekend gatherings, or simply unwinding in the sunshine. Conveniently located just minutes from major highways, shopping, dining, and entertainment, this beautifully renovated home combines modern design with everyday functionality. Schedule your private showing today and experience everything this exceptional property.

2801 Waumpi Trail, Maitland
$324,000
2 Beds ⋅ 2 Baths ⋅ Maitland Harbour Apts SubDv. ⋅ 32751 Zip Code
Offered at a newly improved price, this highly desirable residence at Maitland Harbour is located within a boutique 38-unit lakefront condominium community nestled in the heart of Maitland. Ideally positioned on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—this intimate and picturesque enclave offers access to the entire chain and a truly exceptional waterfront lifestyle. A hidden gem, Maitland Harbour blends timeless Mid-Century Modern architecture with the serenity of lakefront living. Designed by renowned architect Manfred Lopatka, a protégé of Frank Lloyd Wright, and built in 1964, the community reflects a distinctive Central Florida interpretation of classic modernist design. Inside this beautifully updated 2-bedroom, 2-bath residence offering 952 square feet, you will find light-filled living space with a clean, cohesive aesthetic throughout. The kitchen, renovated in 2020, features quartz countertops, a subway tile backsplash, open wood shelving, and a pass-through to the dining area, creating both functionality and visual connection to the main living space. The open-concept living and dining areas are bright and inviting, with warm-toned wood flooring and neutral finishes. The primary suite is a true retreat, complete with updated flooring (2020), soft natural light, newly added barn-style closet doors for improved storage access, and direct access to the private balcony—ideal for enjoying morning coffee or evening breezes. The en-suite bath, renovated by a previous owner, features neutral finishes and a glass-enclosed shower. The secondary bedroom is spacious and offers consistent updated flooring and fresh paint, and is located adjacent to a full guest bath with recent updates including vanity, lighting, and fixtures. Additional improvements include a new refrigerator (2023), new windows (2024), new HVAC (2025), and fresh interior paint (2025/2026). The community has completed major improvements including new roofs, pool enclosure, and exterior paint, and both the milestone inspection and structural integrity reserve study have been completed and are available for review. Residents enjoy a full suite of lakefront amenities including a waterfront pool, courtyard, boat slips, fishing pier, kayak storage, community room, private storage, covered parking, and an expansive entertaining deck overlooking Lake Maitland. The location is adjacent to historic Fort Maitland Park and directly across from Lake Lily, the heart of Maitland’s Cultural Corridor, known for concerts, the Maitland Art Festival, and the Sunday Farmers Market, and is just a short walk to the Enzian Theater and local dining, with easy access to Winter Park’s Park Avenue offering premier shopping, restaurants, museums, and year-round events. Enjoy low-maintenance lakefront living with beautiful interior spaces, a private balcony, and access to one of Central Florida’s most sought-after waterfront settings.

1000 S Orlando Avenue Unit B25, Maitland