Search Results: Single Family Homes in Maitland for Sale

400 S LAKE SYBELIA DRIVE
MAITLAND FL 32751

Residential / Single Family Residence

6 Bed  ·  6 Bath  ·  5,517 SqFt  ·  $344/SqFt

Days on Market: 8

County: Orange
Legal Subdivision Name: METES & BOUNDS
Year built: 1959
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes

Tucked away on over half an acre, this beautifully maintained lakefront home on Lake Sybelia blends modern updates with timeless charm, making it an ideal retreat for those seeking space, comfort, and privacy. Available for the first time in over 45 years, the home has been thoughtfully renovated and expanded over time, resulting in a highly functional layout featuring 6 bedrooms + an office, an elevator, and spacious, sun-filled entertainment areas. The floor plan includes several rooms with lake views, such as the formal dining room, a separate living room, the upstairs owner's suite, and a screened-in front porch. A ... Read more....»

103 W LAKE COLONY DRIVE
MAITLAND FL 32751

Residential / Single Family Residence

5 Bed  ·  5 Bath  ·  4,884 SqFt  ·  $297/SqFt

Days on Market: 110

County: Orange
Legal Subdivision Name: LAKE COLONY PH 01 REP
Year built: 1999
Garage: Yes 3 vehicles
Private Pool: Yes

This gorgeous custom-built, bright and light modern Mediterranean home is in a desirable gated community with tree-lined streets, minutes to Winter Park, Downtown Orlando, Altamonte Mall, I-4, excellent schools, and all the best shops and restaurants. Entertain in the beautiful, completely private backyard, with recently resurfaced lap pool, with pretty Spanish tile. Large master suite with gorgeous brand new spa-like master bath, complete with chandelier. Have fun customizing your brand new his & her closets from the Container Store This home has brand new closet systems in the Jack and Jill upstairs and a new kitchen pantry. Engineered hardwood and tile throughout makes this ... Read more....»

1912 BELFORD COURT
MAITLAND FL 32751

Residential / Single Family Residence

5 Bed  ·  4 Bath  ·  4,266 SqFt  ·  $328/SqFt

Days on Market: 209

County: Orange
Legal Subdivision Name: MAITLAND CLUB REP
Year built: 1997
Garage: Yes 3 vehicles
Private Pool: Yes

Attractively priced! Beautiful custom built SINGLE STORY Mediterranean home nestled at the end of a quiet cul-de-sac in a private gated community with staffed gatehouse! The spacious floor plan accommodates MULTI GENERATION FAMILIES and many guests! Th residence is constructed of concrete block, timeless design, excellent craftsmanship, and a stunning open floor plan which seamlessly flows through classic Palladian doors out to a spacious outdoor living environment - completely covered and screened including a 31' terrace under permanent roof with skylights and oversized salt-water swimming pool and spa! A graceful circular drive leads to covered entry ... Read more....»

858 CRESTON DRIVE
MAITLAND FL 32751

Residential / Single Family Residence

5 Bed  ·  4 Bath  ·  3,785 SqFt  ·  $305/SqFt

Days on Market: 250

County: Orange
Complex/CommunityName: MAITLAND CLUB
Legal Subdivision Name: MAITLAND CLUB REP
Year built: 1996
Garage: Yes 3 vehicles
Private Pool: Yes

New Price!! New Exterior Paint!! Welcome to this beautiful traditional/transitional home that has warm and inviting spaces with upgraded designer touches througout. The open concept floor plan features soaring 13-foot ceilings and great natural lighting. This home has undergone extensive updates while sparing no expense that is reflected in the stunning appointments throughout. Entering the home, you will be embraced by the stately open foyer, living room with great views of the sparkling pool and lushly landscaped backyard, along with the dining /great room area that has tray ceilings and distinguished wainscoting and crown moldings. The chef’s kitchen boasts quartz ... Read more....»

400 W TROTTERS DRIVE
MAITLAND FL 32751

Residential / Single Family Residence

4 Bed  ·  4 Bath  ·  3,189 SqFt  ·  $329/SqFt

Days on Market: 1

County: Orange
Legal Subdivision Name: DELROY PARK
Year built: 1960
Garage: Yes 2 vehicles

One or more photo(s) has been virtually staged. This beautifully updated mid-century home is located in the desirable Delroy Park neighborhood of Maitland, offering the ideal setting for your dream family home. Positioned on a spacious corner lot, this residence blends classic elegance with modern comfort. As you enter, you're welcomed by the timeless beauty of hardwood floors throughout the main living areas, creating a cozy and inviting atmosphere. The open-concept floor plan seamlessly connects the living spaces, making it perfect for both family gatherings and entertaining. The heart of the home is the stunning kitchen, designed for both style and functionality. ... Read more....»

245 W GEORGE AVENUE
MAITLAND FL 32751

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  2,116 SqFt  ·  $447/SqFt

Days on Market: 70

County: Orange
Legal Subdivision Name: REPLAT BLK B POORS ADD
Year built: 1956
Garage: No
Private Pool: Yes

One or more photo(s) has been virtually staged. Discover this beautifully remodeled home located in the heart of Maitland, a highly sought-after community known for its charm, excellent amenities, and top-rated schools. This spacious residence is perfectly situated near Winter Park, providing easy access to a vibrant dining and shopping scene, beautiful parks, and cultural attractions. Fully renovated with brand-new flooring, a modern kitchen, and updated bathrooms, this home combines contemporary upgrades with classic charm, making it truly move-in ready. It features a new fence and additional safety brackets around the pool area, as well as a dedicated BBQ space—perfect for ... Read more....»

51 OAKLEIGH LANE
MAITLAND FL 32751

Residential / Single Family Residence

4 Bed  ·  5 Bath  ·  4,149 SqFt  ·  $227/SqFt

Days on Market: 86

County: Orange
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: OAKLEIGH 3RD ADD
Year built: 1972
Garage: No
Private Pool: Yes

One of the most sought-after Maitland neighborhoods, Oakleigh, on Oakleigh Lane, is tucked back among lakefront estate homes on over a third of an acre. This traditional ranch stretches across all corners with nearly 4,200 square feet and an abundance of outdoor living, providing the ideal backdrop for hosting family and friends. Natural light draws you into a spacious great room with views of the luxurious outdoor pool area that features an in-ground pool surrounded with mature landscaping and brick pavers. The chef’s kitchen showcases a commercial gas range, hood and double oven, built-in refrigerator and breakfast bar overlooking the ... Read more....»

1501 DRUID ISLE ROAD
MAITLAND FL 32751

Residential / Single Family Residence

3 Bed  ·  2 Bath  ·  3,000 SqFt  ·  $308/SqFt

Days on Market: 25

County: Orange
Legal Subdivision Name: DRUID ISLE
Year built: 1971
Garage: Yes 2 vehicles
Waterfront: Yes

NEW YEAR, NEW IMPROVED PRICE Dream Lakeside Living in Maitland! 3 Bed | 2 Bath | Fully Renovated Escape to your perfect sanctuary on the serene shores of Lake Charity! This beautifully updated 3-bedroom, 2-bath home blends modern elegance with timeless charm. From the moment you step inside, you’ll be captivated by: Fully Renovated Interior: Sleek, open-concept design with high-end finishes, luxury flooring, and custom details throughout. Designer Kitchen: Quartz countertops, stainless steel appliances, and a spacious island perfect for entertaining. Spacious Living Areas: Bright, airy rooms with stunning lake views and plenty of natural light. Primary Suite Retreat: A tranquil ... Read more....»

2270 DELORAINE TRAIL
MAITLAND FL 32751

Residential / Single Family Residence

4 Bed  ·  2 Bath  ·  2,000 SqFt  ·  $400/SqFt

Days on Market: 1

County: Orange
Legal Subdivision Name: HIGHLAND PARK ESTATES FIRST ADD
Year built: 1964
Garage: Yes 2 vehicles
Private Pool: Yes

Welcome to 2270 Deloraine Trail, Maitland, FL, located in the established Dommerich - Highland Park Estates community. Professionally renovated by a local interior designer, this 4-bedroom, 2-bathroom pool home flawlessly combines warm modern design with thoughtful functionality. Situated on a corner lot, the home features a side-entry garage, enhancing curb appeal and convenience. The driveway, adorned with pavers and built-in lighting, adds a sophisticated touch to the exterior, ensuring a welcoming first impression. The heart of the home is the stunning gourmet kitchen, showcasing brass and gold luxury fixtures, a convenient pot filler, quartz countertops, and a custom Venetian Plaster wrapped hood. ... Read more....»

2502 CHANUTE TRAIL
MAITLAND FL 32751

Residential / Single Family Residence

4 Bed  ·  2 Bath  ·  2,175 SqFt  ·  $361/SqFt

Days on Market: 150

County: Orange
Legal Subdivision Name: DOMMERICH HILLS 3RD ADD
Year built: 1964
Garage: Yes 2 vehicles
Private Pool: Yes

Price Improvement! **NO HOA** **POOL HOME** Welcome to your dream home in one of Central Florida's most sought-after school district! This luxurious 4-bedroom, 2-bathroom single-story pool home is a masterpiece of modern living. Boasting a brand new roof and AC, this residence spans over 2,100 sqft of meticulously designed space. Step inside to discover an open and airy floor plan that seamlessly integrates the living, dining, and kitchen areas, ideal for both daily living and entertaining guests. The chef-inspired kitchen is a culinary paradise, featuring brand new Samsung appliances, shaker style cabinets, and stunning granite countertops. Every detail of this home has ... Read more....»

251 W HORATIO AVENUE
MAITLAND FL 32751

Residential / Single Family Residence

4 Bed  ·  2 Bath  ·  1,648 SqFt  ·  $455/SqFt

Days on Market: 259

County: Orange
Legal Subdivision Name: OSBORNE MANOR
Year built: 1886
Garage: Yes 1 vehicles

Incredible opportunity to own one of the oldest homes in Maitland. This charming 2-bedroom, 1-bathroom Florida vernacular-style home, built in 1886, sits on a half-acre lot in the heart of Maitland just one home from Lake Sybelia. The original windows, doors, high ceilings and brick street out front give this home so much character, with a large screened-in back porch perfect for relaxing and catching refreshing lake breezes. Out back behind the butterfly garden, you’ll find a small guest cottage, or mother-in-law suite, converted from what was originally a chicken coop in the early 1900s. Notably, the shower of the detached guest cottage has ... Read more....»

1511 E HORATIO AVENUE
MAITLAND FL 32751

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  2,676 SqFt  ·  $271/SqFt

Days on Market: 44

County: Orange
Legal Subdivision Name: MINNEHAHA SHORES
Year built: 1957
Garage: No

One or more photo(s) has been virtually staged. Welcome to this beautifully updated 4 Bedroom, 3 Bathroom home nestled in the heart of Maitland with access to Lake Minnehaha. This inviting property offers a perfect blend of classic charm and modern convenience, ideal for those seeking comfort, style, and space. Walking up, you are first greeted with the circular drive offering ample parking space and the opportunity to add greenery of choice or even holds room for installation of a fountain, etc. Step inside to discover an open-concept layout featuring stunning marble flooring continuing throughout the main parts of the ... Read more....»

1720 ALGONQUIN TRAIL
MAITLAND FL 32751

Residential / Single Family Residence

4 Bed  ·  2 Bath  ·  2,380 SqFt  ·  $294/SqFt

Days on Market: 3

County: Orange
Legal Subdivision Name: DOMMERICH ESTS 1ST ADD
Year built: 1958
Garage: Yes 2 vehicles
Private Pool: Yes

This spacious block home in Dommerich Estates sits on a 0.29-acre lot and offers endless potential for renovation or a complete rebuild. Built by Charlie Clayton, the home features a brick exterior, an oversized two-car garage, and a versatile layout. The original eat-in kitchen connects to a great room that leads to a large Florida room with windows overlooking the pool and a generously sized backyard. The master suite includes terrazzo floors, a walk-in closet, and a shared bathroom that connects to an office, which then leads to a fourth bedroom with its own walk-in closet. Two additional bedrooms, both ... Read more....»

1640 CHINOOK TRAIL
MAITLAND FL 32751

Residential / Single Family Residence

3 Bed  ·  2 Bath  ·  2,091 SqFt  ·  $316/SqFt

Days on Market: 1

County: Orange
Legal Subdivision Name: DOMMERICH WOODS
Year built: 1964
Garage: No

Welcome to the new 1640 Chinook Trail! This open floor plan features a fully remodeled kitchen inclusive of beautiful quartz countertops, shaker cabinets and a brand new Whirlpool appliance kit. The island gives plenty of space to cook or enjoy a meal. Luxury vinyl flooring and fresh paint canvas the interior of the home which is perfect for relaxing or entertaining. Enjoy the luxury of the large primary suite with a spa like bathroom that includes elegant tile work and a double floating vanity. Two other large bedrooms make up the rest of the east wing of the home. New ... Read more....»

1415 CARING COURT
MAITLAND FL 32751

Residential / Single Family Residence

3 Bed  ·  2 Bath  ·  1 Half Bath  ·  2,110 SqFt  ·  $300/SqFt

Days on Market: 21
Cumulative Days on Market: 192

County: Orange
Legal Subdivision Name: ENCLAVE AT MAITLAND
Year built: 2006
Garage: Yes 2 vehicles

Welcome to your beautiful move-in ready home in the highly sought-after gated community in the heart of Maitland. This single-story Mediterranean inspired home boasts three spacious bedrooms, including the grand Primary bedroom suite with its private spa-inspired bathroom, another lovely full bathroom, a convenient half bath, and a separate office or den great for remote work or hobbies. The split-plan allows for plenty of privacy and includes a formal dining room, a chef's kitchen with a lovely eat-in area overlooking the gorgeous family room which leads to the peaceful screened-in back porch. Stunning vaulted ceilings, eight-foot doors, charming archways and ... Read more....»

113 GEM LAKE DRIVE
MAITLAND FL 32751

Residential / Single Family Residence

3 Bed  ·  2 Bath  ·  1,538 SqFt  ·  $374/SqFt

Days on Market: 361
Cumulative Days on Market: 1,285

County: Orange
Legal Subdivision Name: PARK LAKE SHORES
Year built: 1939
Garage: No

Must remodel this 1939 home that was moved from Park Avenue many years ago but now rests in Maitland bordering Winter Park. This home is a piece of history with character but in need of some TLC. Beautifully arched high ceiling along with a fireplace in the formal living room. The Florida room is surrounded by glass sliding doors that open to a wooden patio with French doors, countless windows, gracious screened front porch and additional awning covered porches surrounding the home and huge master bedroom. don't miss this opportunity as large developers have purchased most all properties surrounding this ... Read more....»

2148 CHIPPEWA TRAIL
MAITLAND FL 32751

Residential / Single Family Residence

3 Bed  ·  2 Bath  ·  1,665 SqFt  ·  $342/SqFt

Days on Market: 115
Cumulative Days on Market: 202

County: Orange
Legal Subdivision Name: DOMMERICH HILLS
Year built: 1960
Garage: No
Private Pool: Yes

Welcome to 2148 Chippewa Trail, a charming mid-century modern gem adorned with a newer roof, nestled in the heart of Maitland’s lovely Dommerich Hills neighborhood. This beautifully updated 3-bedroom, 2-bathroom home offers 1,665 square feet of living space with a huge, screened patio and pool area, perfectly blending modern amenities with timeless appeal. Step inside to discover a flowing, open-concept layout featuring vaulted ceilings connecting all of the main living spaces including a stunning kitchen boasting granite countertops, elegant lighting, and a spacious island/breakfast bar waiting for you in the heart of the home. The cozy dining room resides just off of the kitchen, complete ... Read more....»

1910 ROGERS AVENUE
MAITLAND FL 32751

Residential / Single Family Residence

3 Bed  ·  2 Bath  ·  1,706 SqFt  ·  $246/SqFt

County: Orange
Legal Subdivision Name: MAGERSTADT SUB
Year built: 2019
Garage: Yes 2 vehicles

This stunning 3-bedroom, 2-bathroom home, built in 2019, is a modern gem ready for you to call home! This home has an open-concept design featuring gray-tone tile floors, a gorgeous kitchen with shaker-style cabinets, upgraded stainless steel appliances, a large center island, and a closet pantry. The split-bedroom layout offers a serene primary suite with crown molding, a walk-in closet, and an en-suite bath boasting dual sinks and a custom-tiled shower with dual showerheads. Two additional spacious bedrooms share a modern full bath. All bedrooms have brand new carpets installed. The covered lanai and fully fenced backyard with two gates ... Read more....»

240 PEOPLE STREET
MAITLAND FL 32751

Residential / Single Family Residence

3 Bed  ·  2 Bath  ·  1,287 SqFt  ·  $256/SqFt

Days on Market: 136

County: Orange
Legal Subdivision Name: CLARKS ADD
Year built: 1966
Garage: No

Welcome to this beautifully renovated home, boasting three generous bedrooms, 2 full baths and a large bonus room with it's own mini-split AC unit! Upon entering, you will notice how bright this home is, lots of natural light and neutral colors throughout make this house appealing to all decorating styles. The whole house was completely renovated, including kitchen, both bathrooms, roof, electrical, plumbing, windows, water heater and AC in 2022! The kitchen is gorgeous with stainless steel appliances and stunning granite countertops. Are you ready for maintenance free living? This Maitland home is located close to I-4, amazing Winter ... Read more....»

997 HAMLET COURT
MAITLAND FL 32751

Residential / Single Family Residence

3 Bed  ·  2 Bath  ·  1,146 SqFt  ·  $281/SqFt

Days on Market: 56

County: Orange
Legal Subdivision Name: HAMLET AT MAITLAND
Year built: 1996
Garage: Yes 1 vehicles

One or more photo(s) has been virtually staged. Discover Your Serene Retreat in Maitland Welcome to this beautifully renovated home, where modern comfort meets thoughtful design—all for under $350K. With a brand-new roof from 2022, new washer and dryer, and a six-year-old A/C, this home is ready for you to enjoy. The kitchen and bathrooms have been tastefully remodeled in 2024, offering a fresh, contemporary feel. The primary bedroom features an updated layout that enhances flow and includes a spacious closet. You'll love the luxurious primary bath, complete with double vanity quartz counters, shower niche, soaking tub, a soothing rainfall shower head, ... Read more....»

MAITLAND FL 32751

Residential / Single Family Residence

3 Bed  ·  2 Bath  ·  1,076 SqFt  ·  $288/SqFt

Days on Market: 47

County: Orange
Legal Subdivision Name: HAMLET AT MAITLAND
Year built: 1995
Garage: Yes 1 vehicles

Come check out this move-in ready, 3-bedroom, 2-bathroom home with a garage and completely UPDATED and ready for you to move in. The ROOF is only 4 years old! A/C only 4 years old! REPLUMMED in 2020! New WATER HEATER 2021! New FLOORING throughout in 2020! New GARAGE DOOR in 2020! Updated KITCHEN and BATHROOMS in 2020! New CEILING FANS 2020. Everything is done, all you have to do is bring your things! Owner occupied community with a LOW HOA with a pavilion for parties and a playground for the kids. Right in the middle of town and within walking ... Read more....»

1068 HAMLET DRIVE
MAITLAND FL 32751

Residential / Single Family Residence

3 Bed  ·  2 Bath  ·  1,146 SqFt  ·  $270/SqFt

Days on Market: 50

County: Orange
Complex/CommunityName: HAMLET AT MAITLAND
Legal Subdivision Name: HAMLET AT MAITLAND
Year built: 1994
Garage: Yes 1 vehicles

This move-in ready, affordable 3-bed, 2-bath home offers modern comfort and style. Featuring tile throughout, fresh new paint inside and out, and a spacious open living room with high ceilings, this home is perfect for easy living. The kitchen boasts granite countertops and stainless steel appliances. The large primary bedroom includes a walk-in closet and an en-suite bath with two sinks, a shower, and a separate tub. Additional highlights include a newer roof, water heater, and a 1-car garage. Conveniently located just north of Orlando, near highways, top schools, restaurants, and Winter Park shopping! The information recorded in the ... Read more....»

1821 ROGERS AVENUE
MAITLAND FL 32751

Residential / Single Family Residence

3 Bed  ·  1 Bath  ·  960 SqFt  ·  $307/SqFt

New Listing!!!  Days on Market: 1

County: Orange
Legal Subdivision Name: MAGERSTADT SUB
Year built: 1968
Garage: No

Welcome Home!!! Don't lose this opportunity and schedule your showing... This home features 3 bedrooms, 1 bathroom, and an open floor plan with living room, dining room, and kitchen. The kitchen offers beautiful cabinets, stainless steel appliances and granite countertops. Besides been completely remodel it have brand new windows throughout the house and brand-new stucco. Enjoy a big backyard perfect for summer barbecues, family gathering, or creating your own garden oasis. Plenty of space for kids to play and pets to roam! The location is conveniently close to Downtown Maitland, Downtown Winter Park, and easy access ... Read more....»

320 EATON STREET
MAITLAND FL 32751

Residential / Single Family Residence

2 Bed  ·  1 Bath  ·  846 SqFt  ·  $271/SqFt

Days on Market: 94

County: Orange
Legal Subdivision Name: EATONVILLE
Year built: 1945
Garage: No

SELLER TO REPLACE THE ROOF PRIOR TO CLOSING. Welcome to this fantastic 2-bedroom, 1-bath home that has been thoughtfully upgraded throughout. This home comes with an extra space that can be used as a den or an office space. With a new AC unit providing cool comfort and an updated bathroom, this home is move-in ready and worry-free. Seller to replace the roof prior to closing. Outside, a brand new fence encloses the cozy backyard, creating a private retreat for relaxation and enjoyment. Don't miss the opportunity to own this charming home with modern updates and a nice outdoor space.