Maitland Homes For Sale & Real Estate - 132 homes

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 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)

Remarks: Virtually Staged. RARE LAKEFRONT opportunity to Live right on LAKE MAITLAND! Sip your morning coffee with one of the most premier views in the entire community! BONUS: It's on the main FIRST floor, so NO STAIRS! Just a pure unencumbered view of Lake Maitland right from your living room! And only a few steps to the dock or community pool!! This unit has the EXTRA HALF BATHROOM and has been tastefully updated to accentuate it's incredible mid century modern original features, that are in immaculate condition! There may never be another unit quite like this one! The high end plantation shutters offer privacy when needed, but can stay wide open for that view! Enjoy the remodeled Community POOL & Clubhouse all on the stunning water front of Lake Maitland which is also connected to the Winter Park Chain of Lakes. Plenty of fishing, fun and relaxing to be had on the community dock, shuffleboard and putting green! So many amenities nestled amongst the towering shade trees and mature landscaping. The Mid Century Modern architecture is about as timeless of a look that you can find that fits the Maitland/Winter Park lifestyle. You couldn't ask for a better location at just minutes from downtown Winter Park, Park Ave, SunRail station and all the restaurants surrounding the 17/92 Maitland/Winter Park Corridor. All Units recently had metal roof replacement in 2025 and were just freshly painted as well. It's completely move in ready with all New Luxury Vinyl Plank Flooring, Kitchen and bathroom updates,. This unit has not been available for many years, so don't miss out on this view!

Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)

Listing Agent: Christopher Schiffermiller, Llc (407-409-5702)

Remarks: Under contract-accepting backup offers. Bright and well maintained 2 bedroom, 1 bath condo located in a desirable shopping and dining area! This inviting home features abundant natural light, a spacious walk-in closet in the primary bedroom, and a relaxing enclosed patio perfect for additional living space or entertaining. The HOA includes water for added convenience. Residents also enjoy access to a community pool and low-maintenance living close to everything you need. Great opportunity for homeowners or investors alike!

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Brandy Ray (949-449-5652)

Remarks: **ATTENTION INVESTORS** Take advantage of this great opportunity and Add this income producing property to your portfolio with tenant in place. Corner unit 1 bed 1 bath condo with new laminate floors and granite countertops. This second floor unit means there is no one above you and has a pool view located steps away. The mailbox and pool are only a few steps away. Location is walking distances to Publix, Starbucks and many other stores. It is also just a 10 min drive to Full Sail University and a 30 minute drive to the parks. Best location in Orlando! Best Return available!

Listing is courtesy of: MAYOLET REALTY LLC (407-491-4893)

Listing Agent: Mayolet Bornas Moreira (407-491-4893)

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)

Remarks: Back on the market through no fault of the property. Recently appraised at $340,000 and inspections were completed without issue. A great opportunity for a qualified buyer seeking a smooth transaction and quick closing. Tucked into one of Maitland's most coveted lakefront enclaves, this beautifully updated townhome sits within a quietly maintained, tree-lined setting with direct access to Lake Destiny, a private community boat ramp, resort-style pool, and tennis courts, all just minutes from I-4, the 414, RDV Sportsplex, and the dining and shopping corridors of Maitland Center. First impressions set a private and secluded tone with a wrought-iron gated courtyard leads to a covered entry porch before you reach the front door. Inside, soaring vaulted ceilings and a dramatic arched transom window above the sliding glass doors flood the main level with natural light, creating an airy, open feel that far exceeds the square footage on paper. Wide-plank tile flooring runs throughout the main living areas, connecting the open living and dining spaces to a thoughtfully updated kitchen featuring white shaker cabinetry with crown accents, solid stone countertops, stainless steel appliances including a French door refrigerator and built-in microwave, pendant lighting above the breakfast bar peninsula, and a subway tile backsplash. The sliding doors open directly to a private screened patio framed by mature landscaping, creating the kind of indoor-outdoor flow that defines Florida living at its best. Upstairs, three generously sized bedrooms each offer ceiling fans, ample closet space, and brand new carpet and paint. The primary suite stands out with a 26ft footprint, two closets including a walk-in, and an ensuite bath featuring dual vanities, a full-wall vanity mirror, and a walk-in shower. Two additional bedrooms and a full bath complete the upper level, with the layout providing genuine separation and privacy between spaces. Back on the main floor, a versatile 9x9 bonus room with indoor laundry handles the day-to-day, and the full-size washer and dryer convey. The big-ticket items are handled: 30-year tile roof replaced in 2023, HVAC installed in 2020, and brushed nickel fixtures updated throughout. The one-car garage with additional driveway parking and the gated courtyard entry give this unit a sense of privacy and security rare in townhome living. Whether you are looking for a low-maintenance primary residence, a lock-and-leave second home, or a smart investment in a well-managed community with real amenities and a lakefront address, this one makes an easy case.

Listing is courtesy of: DON HARKINS REALTY LLC (321-377-0341)

Listing Agent: Donald Harkins, Iii (321-377-0341)

Remarks: Under contract-accepting backup offers. Perfectly positioned between Maitland and Winter Park, this beautifully maintained 3-bedroom, 2.5-bath pool home offers an exceptional combination of charm, character, and an unbeatable location just minutes from the shops and restaurants of Park Avenue. Warm hardwood floors flow throughout the home, while the impressive two-story family room showcases soaring ceilings and a wood-burning fireplace that creates a welcoming gathering space. Separate living and dining rooms provide flexibility for both everyday living and effortless entertaining. The kitchen is thoughtfully designed with newer stainless-steel appliances and opens to the family room. French doors invite you outside to a private backyard retreat, while the adjacent sunroom is the perfect place to enjoy morning coffee with peaceful views of the pool and lush landscaping. Upstairs, you'll find three spacious bedrooms and two beautifully renovated baths. The primary suite is filled with natural light from a charming bay window and features a spa-inspired bath with marble floors, quartz countertops, dual vanities, and timeless subway tile. Step outside to your own backyard oasis. The covered lanai, complete with a summer kitchen, overlooks a newer saltwater pool and an expansive brick patio, creating the ideal setting for year-round outdoor living, entertaining, or simply unwinding in a private, tranquil setting. Adding to its appeal, the home is located just one house from the Winter Park city limits and is zoned for highly acclaimed Dommerich Elementary, Maitland Middle, and Winter Park High School. Enjoy the convenience of nearby Lake Lily, Enzian Theater, Maitland City Centre, and the boutiques, dining, and vibrant lifestyle of Winter Park's famed Park Avenue. This home offers the rare opportunity to enjoy a peaceful neighborhood setting with the very best of Maitland and Winter Park just moments away.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Wendy Williams Crumit (321-356-8590)

Remarks: 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 hot water heater and the electrical panel upgraded within the past couple of years. This wonderful unit is at a great price and will not last long.

Listing is courtesy of: NEXTHOME NEIGHBORHOOD REALTY (407-377-7735)

Listing Agent: Warren Gagne (407-461-9120)

Remarks: Sought-after Visconti community of Maitland. The lowest 2-2 entry point currently available. This third-floor, 2-bed, 2-bath, 1,048 sqft condo features updated flooring, designer paint, LED lighting, new ceiling fans, updated faucets, and a screened patio with exterior storage. Community amenities include two pools overlooking Lake Shadow, tennis courts, lakeside walking paths, dog stations, and car wash stations, minutes to I-4, 429, downtown Orlando. Sold as-is, priced to sell.

Listing is courtesy of: JOSEPH WALTER REALTY LLC (248-294-7850)

Listing Agent: Scott Fader (248-294-7850)

Remarks: A rare 4 BR condo with A rated High School could be your next home. Visconti is a high end luxury community featuring a huge lakeside pool with beach entry, fitness center that rivals many commercial gyms, tennis courts, walking paths, and a fantastic clubhouse. The 2nd floor condo has an extremely functional layout that separates the master BR from the other 3 bedrooms. The kitchen is stunning with updated cabinets, solid surface counters and a gorgeous back splash. The common areas feature wood laminate floors with carpet in the bedrooms. Conveniently located in Maitland, this homes is just minutes away from restaurants, shops, I4, 414, and the Maitland business center. A fantastic choice for your main home, a 2nd home or an addition to a rental portfolio.

Listing is courtesy of: INFINITY REAL ESTATE GROUP (407-760-0835)

Listing Agent: Christopher Paul (321-277-7609)

Remarks: Under contract-accepting backup offers. Big vibes and even bigger possibilities! Say Hello to easy Florida living! This stylish 4-bedroom, 2-bath Maitland home delivers bright natural light, functional living spaces, and room for everyone to spread out. Whether you’re hosting game nights, working from home, or enjoying quiet mornings with coffee on the patio, this home checks all the boxes. A backyard perfect for entertaining and soaking up the sunshine! Prime location close to everything Central Florida has to offer! This one is ready to impress!

Listing is courtesy of: SYNCHRONICITY REAL ESTATE SOLUTIONS (407-617-2378)

Listing Agent: Michelle Terry (407-617-2378)

Remarks: Under contract-accepting backup offers. Tucked away in the heart of Maitland, this thoughtfully updated three-bedroom, two bath residence blends everyday comfort with meaningful, modern upgrades. Freshly painted interior (June 2026) and a private spa pool WITH BRAND NEW POOL PUMP creates a serene outdoor retreat—perfect for unwinding or entertaining year-round in true Florida style. Inside, the home offers both function and peace of mind with a dedicated laundry room featuring a brand-new washer (2026) and newer dryer (2024). Major system updates have already been taken care of, including a new water heater (2025) and a recently installed HVAC system (April 2026), providing efficiency, reliability, and confidence from day one. Ideally located with close proximity to I-4 for easy commuting, and just a short walk to Maitland Community Park and Lake Lily, this home offers the perfect balance of convenience and lifestyle. A move-in-ready opportunity where the essential upgrades are already done for you.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Sarah Tomlinson (407-721-7823)

Remarks: Under contract-accepting backup offers. Tucked between the shores of Lake Nina and Lake Maitland, this beautifully reimagined California ranch blends modern design with effortless everyday living in one of Maitland’s most desirable locations. Completely remodeled in 2022, the home showcases a fresh, sophisticated aesthetic with thoughtfully curated finishes throughout. The light-filled interior offers seamless flow between living spaces, combining clean modern lines with warm, inviting character. The renovated kitchen features a brand-new range, oven, and microwave, creating a stylish and functional centerpiece for both entertaining and daily life. Custom closets throughout the home provide elevated organization and exceptional storage. In addition to the main living areas, a spacious bonus room offers incredible flexibility and can easily function as a second family room, home office, fitness studio, playroom, or media space to fit your lifestyle needs. Step outside to a private backyard retreat designed for entertaining, complete with a sparkling pool, expansive outdoor living space, and plenty of room for gatherings, dining, and relaxing under the Florida sunshine. The indoor-outdoor flow perfectly captures the essence of California-inspired living. Ideally positioned in a picturesque pocket of Maitland between two beautiful lakes, this home also benefits from zoning for top-rated schools while offering convenient access to dining, shopping, parks, and major roadways. A rare opportunity to enjoy modern California-inspired living in an exceptional location.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Sarah Tomlinson (407-721-7823)

Remarks: Virtually Staged. Exceptional value meets timeless elegance in this incredible home nestled in the heart of Maitland, privately situated on a cul de sac within an exclusive gated enclave of custom residences. The Saltwater pool has a brand new sparkling finish! Perfectly positioned between Lake Sybelia and Lake Catherine, this one owner estate offers a rare blend of sophistication, comfort, and versatility with five spacious bedrooms, four and a half baths, and a three car garage, complemented by soaring ceilings, refined architectural details, and a thoughtfully designed open layout. The gourmet kitchen features solid wood cabinetry, a large island, newer refrigerator, walk in pantry, and dual breakfast bars that seamlessly connect to the formal dining and family rooms, where a cozy gas fireplace and a bar with sink and ice icemaker, create an inviting setting for everyday living and entertaining. Designed with flexibility in mind, this home effortlessly adapts to your family’s needs, ideal for traditional living, multigenerational arrangements, a private guest retreat, or a dedicated work from home environment with two wings on the first level. Upstairs, the luxurious owner’s retreat provides a peaceful escape with a loft style office and sitting area, dual walk in closets, and a spa inspired bath. Outdoors, enjoy a lush tropical setting featuring a saltwater pool with new equipment, along with papaya trees and blooming amaryllis that create a serene, resort-style atmosphere. Additional highlights include a new roof (2023), first floor laundry with newer appliances, tray ceilings, elegant archways, all just minutes from top rated schools, parks, dining, shopping, Winter Park’s Park Avenue and the Winter Park Village as well as many local favorites, offering the perfect combination of privacy, convenience, and endless possibilities to create a space that truly reflects your lifestyle. Enjoy scenic walkability or a bike ride along Lake Sybelia to local cafés, the Sunday Farmers Market, and the Maitland Art Museum in one of Central Florida’s most sought after communities. Schedule your private showing today and experience the extraordinary lifestyle this Maitland home provides.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Jo Ann Lamar (321-231-0052)

Remarks: Amazing upgraded two-bedroom, one bath Condo in the gated waterfront community at Visconti in Maitland with features of spacious living and comfortability. This stunning Condo Unit features with large windows letting in plenty of natural light and giving the common living area a fresh air feel. The dining/living combo opens to a big, screened patio through sliding glass doors. The kitchen overlooks the living and dining room and contains a full suite, including the refrigerator, range, dishwasher, disposal and plenty of cabinet and countertop. The bedroom is also including a large walk-in closet. This unit has oversized laundry room that includes full-size washer and dryer.Visconti community comes with professional maintenance of Ponds, professionally landscaped and well-maintained common areas as well as a BEAUTIFUL Resort Style Pool and Club House along with tennis court, fitness, basketball court, car washing area ext. Primely located close to all shopping, entertainment areas and just minutes to major highways, I4. You don't need to look any further for your Dream Home! Schedule your viewing today! Note: Some of the pictures are showing the virtual staging of the unit and the furnitures are not included to the listing

Listing is courtesy of: USCO CAPITAL GROUP (407-666-7686)

Listing Agent: Simon Colak (407-666-7686)

Remarks: Substantial price reduction for LAKESIDE LIVING in Maitland, Florida! LEASE OPTION CONSIDERED! Nestled canal front with direct access to Lake Charity, this vintage block home is built like a fortress with all the modern luxuries of today. A unique home for those who desire authenticity in both design and quality. A side entry garage leads to a courtyard like entrance with a marble path and asian influenced landscape. Double doors open into an expansive footprint with 3 large bedrooms, 2 baths and over 3,000 sq ft of living space. A 42 x 12 sunroom overlooking the water pays homage to the nostalgic Florida charm of this decade. No expense was spared when renovating this interior. Luxurious finishings and professional installation can make all the difference! Especially noted in the kitchen and baths! Upon entering, a Balsato Beige Porcelain fireplace surround wall anchors the space with plenty of areas to create conversational seating, a designer’s dream! The kitchen island is open to the entire living space with tons of storage and a double waterfall edge in Taj Mahal Quartzite. The perimeter counters are done in beautiful Bora Bora Quartz by Sharifstone. Real wood cabinetry in white dove compliments the earth tones giving a more transitional than modern vibe. Brushed gold hardware, lighting & plumbing fixtures are the perfect “jewelry” for the space! All new high end appliances convey. A brick fireplace graces the dining/living room wall (sounding like a song), yet another functional design opportunity to really create a home that works for YOU. There’s plenty of spots for an office, although not formally mentioned and the ability to use some of the square footage to create an additional “room” if needed. The primary suite closet takes the cake with all the fun features a dream closet should have! The ensuite bath has a lovely vanity with Quartz tops, dual sinks and a gorgeous shower with designer tile and a frameless glass door. Hardware is all in a matte black. The additional 2 bedrooms share a bath that has also had a complete remodel! This home is move in ready with a timeless style throughout. Flooring is a cohesive blend of tile and luxury vinyl plank. New roof 2024. With ideal proximity to fine dining & shopping in Maitland, Winter Park’s infamous Park Avenue and the Theme Parks, you’ll find yourself “staycationing” a little more often!

Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)

Listing Agent: Autumn Makin (352-455-0044)

Remarks: Sensational ALL-Block Home in Maitland with NO HOA and Deeded Private Lake Access! Nestled within Lakewood Shores, a charming and  welcoming enclave of 42 homes, this 3BR/2BA residence offers a leisurely lifestyle with deeded access to Lake of the Woods via private neighborhood boat ramp. Venture inside to discover an openly flowing traditional layout, soft natural light, well-equipped kitchen w/skylights, separate dining area, and a cozy living room with a wood-burning fireplace. Each bedroom is generously-sized, while the primary bedroom has an en suite w/step-in shower. Enjoy the entertaining possibilities of the screened-in lanai, as well as the fenced-in backyard boasting a shed with electricity connected. Other features: attached carport w/newly epoxy floors, indoor laundry area, new electrical service panel, updated windows/plumbing/water heater, cost-savings well sourced irrigation system, near Maitland Art Center, Lake Lily Park, and the Enzian Theater, close to Downtown Maitland, Park Avenue, Winter Park Village, I-4, and much more! Call and schedule your private showing today!

Listing is courtesy of: BESPOKE REAL ESTATE (407-476-7647)

Listing Agent: Todd Norwood (407-733-1491)

Remarks: Under contract-accepting backup offers. Discover a beautifully transformed 4-bedroom, 2-bath Maitland gem, a turnkey showpiece that blends modern style, smart upgrades, and undeniable curb appeal. The home greets you with a fresh look, mature landscaping, manicured hedges, and a custom front deck with modern horizontal railing, creating a welcoming entry and the perfect spot to enjoy your morning coffee. Step inside to an open and airy layout with abundant natural light, wood-look flooring, updated lighting fixtures, and multiple living areas ideal for both everyday living and entertaining. The renovated kitchen features white shaker cabinetry, modern countertops, stylish backsplash details, stainless steel appliances, and ample cabinet space. The dishwasher and oven were recently updated between 2022 and 2024. The kitchen flows seamlessly into the dining and living areas, creating a functional and inviting layout. The home offers spacious bedrooms along with versatile flex spaces perfect for a home office, guest room, or additional living area. The primary suite includes an updated ensuite bathroom with a glass-enclosed walk-in shower and a custom-designed primary closet with built-in organization. Out back, enjoy a fully refreshed backyard featuring brand new sod, a brand new paver patio, and a covered, screened back porch ideal for relaxing or entertaining year-round. Additional upgrades include a brand new driveway, solar panels for energy efficiency (to be paid off in full by the sellers at closing upon an accepted offer), smart home features, updated bathrooms, and modern finishes throughout. Adding to the appeal, HOA membership is optional, offering buyers the freedom of homeownership without mandatory HOA dues or restrictions. Conveniently located near shopping, dining, parks, and major roadways, this beautifully maintained Maitland home combines comfort, functionality, and contemporary style in one of Central Florida's most desirable communities.

Listing is courtesy of: ALPHA EQUITY REALTY & MANAGEMENT INC (407-789-1002)

Listing Agent: Abbas Sultanali (407-435-9596)

Remarks: Experience resort-style living in the heart of Maitland at the highly desirable gated community of Visconti. This beautifully maintained three-story townhome offers 1,280 square feet of thoughtfully designed living space plus an oversized attached garage, providing the perfect combination of comfort, functionality, and low-maintenance living. The open-concept main living level features luxury vinyl flooring, soaring ceilings, abundant natural light, and a spacious kitchen with stainless steel appliances, updated countertops, tile backsplash, breakfast bar seating, and generous cabinet space. The spacious primary suite offers a large walk-in closet and private bath, while the additional bedrooms provide flexibility for guests, a home office, or growing families. A full-size interior laundry room, ample storage, and neutral finishes make this home truly move-in ready. Visconti residents enjoy an impressive collection of amenities including a gated entrance, resort-style swimming pool, a state-of-the-art fitness center, playground, scenic walking paths, car wash station, and beautifully landscaped grounds shaded by mature oak trees. Conveniently located just minutes from I-4, Winter Park, Downtown Orlando, AdventHealth, RDV Sportsplex, shopping, dining, and entertainment, this home offers the perfect blend of convenience, lifestyle, and value.

Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)

Listing Agent: Patricia Sullivan (407-719-6550)

Remarks: Great opportunity to own this 1-bedroom, 1-bathroom first-floor unit in a desirable and well-maintained community! This property offers a comfortable and functional layout with easy first-floor access, perfect for both homeowners and investors alike. Currently tenant-occupied with a lease in place through June 30, 2026, providing immediate rental income with future flexibility for personal use. Residents enjoy access to excellent community amenities, including a sparkling pool, fitness center, and playground, all within a lovely and welcoming environment. Conveniently located near major highways, shopping, dining, and entertainment, this property offers both lifestyle and investment potential. Don’t miss this versatile opportunity!

Listing is courtesy of: MIAMI TANGO INVESTMENTS REALTY (786-464-8803)

Listing Agent: Moses Nae (407-499-0240)