Maitland, FL Homes for Sale with Parking

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  /52

  $774,900

  • 3 Beds
  • 2.5 Baths
  • 2,441 Sq Ft

  312 Macarthur Place, Maitland, FL 32751

  NEW ROOF, NEWER AC, and NO HOA—this beautifully maintained home on a quiet cul-de-sac offers comfort, charm, and an unbeatable location. Nestled just steps from Lake Sybelia. This property provides a peaceful, scenic setting while still being close to all that Maitland has to offer, including popular local restaurants, shops, and community spots. A short drive takes you to the vibrant dining,

  Sean David REAL BROKER, LLC

  312 Macarthur Place, Maitland, FL 32751
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  /31

  $784,000

  • 3 Beds
  • 3.5 Baths
  • 2,407 Sq Ft

  1732 Ridgewood Ave Unit S, Maitland, FL 32751

  This custom two-story townhome delivers what most properties in this category simply don’t; space, light, and a layout that actually makes sense. Open, airy, and thoughtfully designed, every detail feels intentional. Perfectly positioned between Maitland and Winter Park, you’re just minutes from Park Avenue, Winter Park Village, and some of the best dining and shopping in Central Florida. Step

  Brandon Geers COMPASS FLORIDA LLC

  1732 Ridgewood Ave Unit S, Maitland, FL 32751
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  /48

  $555,000

  • 4 Beds
  • 3 Baths
  • 1,857 Sq Ft

  2570 Derbyshire Rd, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Welcome to 2570 Derbyshire Blvd, a fully transformed 4-bedroom, 3-bathroom Maitland pool home where modern design meets effortless Florida living. This top-to-bottom renovation delivers both style and tranquility, featuring a brand-new 2026 roof, all-new windows, and a newly refinished pool. Inside, the heart of the home is the stunning designer

  Nelson Folchini WRA BUSINESS & REAL ESTATE

  2570 Derbyshire Rd, Maitland, FL 32751
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  /54

  $3,299,000

  • 5 Beds
  • 4.5 Baths
  • 4,819 Sq Ft

  350 Northwind Rd, Maitland, FL 32751

  Nestled within the 9-acre Lake Maitland Owl Preserve, this striking contemporary residence—crafted by acclaimed green builder E2 Homes offers a rare blend of architectural distinction, privacy, and natural beauty. Surrounded by protected conservation land, the home delivers a serene retreat just minutes from the vibrant lifestyle of Winter Park. Designed by internationally recognized architect

  Lianna D'Angelo SOTERA LIVING

  350 Northwind Rd, Maitland, FL 32751
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  /30

  $415,000

  • 3 Beds
  • 3.5 Baths
  • 2,103 Sq Ft

  1994 Kenaston Rd Unit 1994, Maitland, FL 32751

  Located in the desirable city of Maitland, just three miles from Winter Park’s renowned Park Avenue, this extensively updated 3-bedroom, 3.5-bath townhouse offers modern living in a prime Central Florida location. Tucked within a quiet residential setting and zoned for highly rated Seminole County schools, the home provides easy access to dining, shopping, and entertainment while maintaining a

  Veronica Figueroa EXP REALTY LLC

  1994 Kenaston Rd Unit 1994, Maitland, FL 32751
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  /36

  $895,000

  • 4 Beds
  • 4 Baths
  • 2,995 Sq Ft

  310 White Oak Cir, Maitland, FL 32751

  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

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  310 White Oak Cir, Maitland, FL 32751
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  /47

  $795,000

  • 2 Beds
  • 2 Baths
  • 1,685 Sq Ft

  1100 S Orlando Ave Unit 956, Maitland, FL 32751

  LAKEFRONT - Enjoy condo living at its finest from the top-floor Lake Maitland penthouse with million-dollar water and above treetop views, and beautiful panoramic sunrises from multiple rooms. This 9th-floor, 1,685 SF residence features 2 bedrooms, 2 baths, 2 multi-purpose rooms, and an open-concept kitchen, dining, and living area. Centered on the west cove of Lake Maitland, the largest of the

  Joann Beck BECK REALTY LLC

  1100 S Orlando Ave Unit 956, Maitland, FL 32751
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  /43

  $1,225,000

  • 4 Beds
  • 3 Baths
  • 2,292 Sq Ft

  67 Cypress Ln, Maitland, FL 32751

  Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths.Step inside to discover hardwood floors flowing

  Kelly Price KELLY PRICE & COMPANY LLC

  67 Cypress Ln, Maitland, FL 32751
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  /27

  $489,990

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft

  2065 Derbyshire Rd, Maitland, FL 32751

  Beautifully renovated and move-in ready, this 3-bedroom, 2-bath home offers modern design in a .24 acre lots, solid upgrades, and comfortable living in a prime Maitland location. Featuring an open-concept layout filled with abundant natural light, the home delivers a warm and inviting atmosphere from the moment you enter. The updated kitchen serves as the heart of the home, showcasing sleek

  Ceila Morales EXP REALTY LLC

  2065 Derbyshire Rd, Maitland, FL 32751
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  /22

  $585,000

  • 4 Beds
  • 2 Baths
  • 1,959 Sq Ft

  2453 Worthington Rd, Maitland, FL 32751

  A lovely well designed 4bdr. 2 bath home with an eat in kitchen open to a spacious family rm. A formal din.rm. and formal lvg.rm. are ready for any occasion. The long 2 lane brick driveway can accommodate multiple vehicles. Nearby schools for all levels and the amenities for recreation and entertainment are too numerous to list. This house should be added to your list when searching for your new

  Stephen Hachey REALTY OF RIVERVIEW LLC

  2453 Worthington Rd, Maitland, FL 32751
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  /50

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 1,734 Sq Ft

  223 Quayside Cir Unit C, Maitland, FL 32751

  Welcome to refined living in The Moorings! This beautifully updated 3-bedroom, 2.5-bath townhouse offers 1,734 square feet of thoughtfully designed space in one of Maitland's most sought-after communities. The open layout showcases soaring ceilings and gleaming engineered wood floors throughout, creating an inviting atmosphere filled with natural light.The heart of the home is a stunning

  Kelly Price KELLY PRICE & COMPANY LLC

  223 Quayside Cir Unit C, Maitland, FL 32751
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  /59

  $1,100,000

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  1421 Sunnyside Dr, Maitland, FL 32751

  One or more photo(s) has been virtually staged. HUGE PRICE IMPROVEMENT Welcome to 1421 Sunnyside Drive, Maitland, FL, a beautifully maintained 4-bedroom, 2.5-bath single-family home with a pool, located on a corner lot directly adjacent to Winter Park. While this home carries a Maitland address, it sits just steps from Winter Park homes, offering the best of both locations. This move-in-ready

  Amanda Binns STRICKLAND REALTY GROUP INC

  1421 Sunnyside Dr, Maitland, FL 32751
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  /36

  $895,000 Open Sat 11AM - 1PM

  • 2 Beds
  • 2.5 Baths
  • 1,459 Sq Ft

  219 Quayside Cir Unit B9, Maitland, FL 32751

  Every so often, a property comes along that redefines what lake living can be, and this is that home. Thoughtfully reimagined from top to bottom, this two-bedroom, two-and-a-half-bath residence blends refined design with the effortless lifestyle of the Winter Park Chain of Lakes. Go inside to discover a fully renovated interior anchored by a showstopping 14-foot Cambria quartz waterfall island,

  Chad Isenhart PREMIER SOTHEBY'S INTL. REALTY

  219 Quayside Cir Unit B9, Maitland, FL 32751
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  /28

  $225,000

  • 2 Beds
  • 1.5 Baths
  • 1,353 Sq Ft

  1009 Grove St Unit 1009, Maitland, FL 32751

  This beautifully updated 2 bedroom, 1.5 bath condo in Maitland is located minutes from shops, restaurants and offers easy access to I-4!. The stylish kitchen features granite countertops, 42 inch cabinetry, built-in wine glass rack, stainless appliances, pass thru window, and a long breakfast bar. Updated half bath downstairs for convenience. Both spacious bedrooms are located upstairs and share

  Ingrid Livingston COLDWELL BANKER REALTY

  1009 Grove St Unit 1009, Maitland, FL 32751
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  /21

  $335,000

  • 2 Beds
  • 2 Baths
  • 1,177 Sq Ft

  2344 Sierra Ln, Maitland, FL 32751

  Price improved! CONDO WITH PRIVATE GARAGE - JUST REPLUMBED WITH WARRANTY! Discover the perfect blend of comfort, elegance, and convenience in this beautifully updated 2-bedroom, 2-bath condominium in the highly sought-after Sierra Condominiums of Maitland. This move-in ready condo welcomes you with a screened front porch and an inviting living room with a wood-burning fireplace with an electric

  Kathy McDonald WATSON REALTY CORP

  2344 Sierra Ln, Maitland, FL 32751
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  /39

  $595,000

  • 3 Beds
  • 2.5 Baths
  • 1,734 Sq Ft

  225 Quayside Cir, Maitland, FL 32751

  Discover the perfect blend of style and location in this beautifully updated 3-bedroom, 2.5-bathroom townhome in the sought-after Moorings community. With 1,734 square feet of thoughtfully designed living space, this residence offers a bright, open floor plan enhanced by vaulted ceilings and an abundance of natural light.The heart of the home is the stunning kitchen, showcasing white

  Kelly Price KELLY PRICE & COMPANY LLC

  225 Quayside Cir, Maitland, FL 32751
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  /21

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft

  204 Quayside Cir Unit 304, Maitland, FL 32751

  SELLER PAYING CONCESSIONS OF 6 MONTH HOA FEES. Something is very special about Lakefront Living! Come visit this beautiful Lakefront Condo located at The Moorings On Lake Maitland, part of the Winter Park chain of lakes. Enjoy the Florida lifestyle in a carefree home with lake front amenities. Imagine Entertaining Family & Friends at the Pool or Heated Spa and the Clubhouse of the Moorings on

  Beatrice Palladino GALLERY PROPERTIES INTERNATIONAL

  204 Quayside Cir Unit 304, Maitland, FL 32751
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  /19

  $525,000

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft

  204 Quayside Cir Unit 604, Maitland, FL 32751

  Penthouse Living at The Moorings on Lake Maitland – 204 Quayside Cir #604Welcome to your dream home in the highly desirable community of The Moorings on Lake Maitland. This rarely available 2 bed/2 bath penthouse unit truly offers a exceptional blend of comfort, style, and location in the heart of one of Central Florida’s most sought-after lakefront communities. Entering the unit just steps

  Francis Gilman KELLER WILLIAMS WINTER PARK

  204 Quayside Cir Unit 604, Maitland, FL 32751
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  /50

  $1,100,000

  • 5 Beds
  • 3.5 Baths
  • 4,144 Sq Ft

  791 Sequoia Trail, Maitland, FL 32751

  Discover a rare opportunity in Dommerich Woods, a distinguished and established Maitland neighborhood celebrated for its rich heritage. Situated on .33 acre of lushly landscaped grounds, this remarkable property welcomes with paver drive and enjoys a tranquil setting along apeaceful creek connecting Lake Minnehaha and Lake of the Woods - creating an atmosphere of natural elegance and

  David Van Wormer VANWORMER REALTY & DEVELOPMENT

  791 Sequoia Trail, Maitland, FL 32751
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  /20

  $308,000

  • 3 Beds
  • 2 Baths
  • 1,076 Sq Ft

  1074 Hamlet Dr, Maitland, FL 32751

  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

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  1074 Hamlet Dr, Maitland, FL 32751
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  /19

  $529,000

  • 4 Beds
  • 2.5 Baths
  • 1,939 Sq Ft

  1695 E Horatio Ave, Maitland, FL 32751

  Great Location, this home is located on Community of Dommerich Estates, Maitland, Florida, No HOA, Top Rated Shools, less than 1 mile to Lake Minnehaha and approximately 2.6 miles to Lake Maitland, and less than 1 mile to John Langdon Park, John Hudson Park, and Kings Row Park. House is just revitalized with a new fresh interior Stone Eagle Color Paint, Roof replaced in 2024, AC replaced in 2022,

  Tuan Nguyen VISTA REALTY INVESTMENT

  1695 E Horatio Ave, Maitland, FL 32751
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  /56

  $1,395,500

  • 5 Beds
  • 4.5 Baths
  • 4,566 Sq Ft

  755 Cranes Ct, Maitland, FL 32751

  One or more photo(s) has been 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. Perfectly positioned between Lake Sybelia and Lake Catherine, this one owner estate offers a rare blend of sophistication, comfort, and versatility with five

  Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

  755 Cranes Ct, Maitland, FL 32751
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  /54

  $320,000

  • 3 Beds
  • 2.5 Baths
  • 1,583 Sq Ft

  2329 Shadow View Cir, Maitland, FL 32751

  Welcome to this stunning, fully renovated 3-Bedroom, 2.5-Bath home located in the desirable Visconti community of Maitland. This beautifully updated 3-bedroom, 2.5-bathroom unit offers over 1,580 sq ft of modern living space, featuring luxury finishes and an open-concept layout perfect for both entertaining and everyday living with brand-new flooring, fresh paint, and upgraded fixtures

  Julian Carvajal LPT REALTY, LLC

  2329 Shadow View Cir, Maitland, FL 32751
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  /53

  $1,700,000

  • 5 Beds
  • 4 Baths
  • 4,814 Sq Ft

  255 W George Ave, Maitland, FL 32751

  Experience the blend of timeless elegance and modern luxury in this Maitland estate a block away from Lake Sybelia. Completely renovated in 2007, every detail of this home exudes sophistication. A spacious paver driveway leads to a two-car garage, framed by lush tropical landscaping, decorative stone accents, and a charming fountain, creating an inviting first impression. The grand foyer welcomes

  Peter Luu REAL BROKER, LLC

  255 W George Ave, Maitland, FL 32751
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  /34

  $1,800,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,567 Sq Ft

  1130 Mechanic St, Maitland, FL 32751

  Pre-Construction. To be built. Come build your dream home on this exceptional homesite in the heart of Maitland.This stunning new construction single-family residence will feature 4 bedrooms, 4.5 bathrooms, and 3,567 square feet of thoughtfully designed living space across two stories, showcasing sleek modern finishes and open-concept living ideal for today’s lifestyle. Set on a 0.26-acre

  Richard Palmano PALMANO GROUP RE BROKERAGE LLC

  1130 Mechanic St, Maitland, FL 32751
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  /16

  $1,798,999 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,203 Sq Ft

  105 Tangelo Ct, Maitland, FL 32751

  Under Construction. A masterpiece of luxury design by LUIH Luxury Homes, perfectly positioned in the prestigious neighborhood of Hollieanna Shores. As you arrive, a striking façade with an elegant arched entryway sets an unforgettable tone. Beyond the front door, soaring ceilings and designer finishes frame an expansive living room where glass sliders dissolve the boundary between indoor and

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  105 Tangelo Ct, Maitland, FL 32751
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  /18

  $369,000 Pre-Foreclosure

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft

  361 Hickory Dr, Maitland, FL 32751

  One or more photo(s) has been 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

  Emma Nelson KELLER WILLIAMS REALTY AT THE PARKS

  361 Hickory Dr, Maitland, FL 32751
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  /31

  $879,900 Pre-Foreclosure

  • 5 Beds
  • 4 Baths
  • 2,966 Sq Ft

  1135 Thunder Trail, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Dommerich Hills Pool Home | Oversized Lot | No HOA Tucked into the highly sought-after Dommerich Hills neighborhood, this beautifully updated pool home offers the kind of space, charm, and lifestyle that’s becoming harder to find in Maitland. Sitting on an oversized lot with no HOA, the home provides nearly 3,000 square feet of thoughtfully designed

  Angela Worachek DALTON WADE INC

  1135 Thunder Trail, Maitland, FL 32751
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  /15

  $304,999

  • 3 Beds
  • 1.5 Baths
  • 1,162 Sq Ft

  551 Ruffel St, Eatonville, FL 32751

  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

  Buffy Barrott RESIDENTIAL MATCHMAKERS LLC

  551 Ruffel St, Eatonville, FL 32751
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  /65

  $2,450,000

  • 4 Beds
  • 5 Baths
  • 5,051 Sq Ft

  2550 Venetian Way, Winter Park, FL 32789

  Chain of Lakes Water- Front Home with Private Boat Dock, Winter Park Luxury Living. Step into your future with this extraordinary custom built residence, inspired by the artistic richness of Fernando Botero. From your back lanai, step directly onto your private, custom boat dock featuring a covered, remote-operated boat lift, and cruise the Venetian Canal with direct access to WinterPark’s

  Felicia Donateli PALM PROPERTIES OF CF, INC.

  2550 Venetian Way, Winter Park, FL 32789
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  /29

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,020 Sq Ft

  2900 Oranole Rd, Orlando, FL 32810

  Welcome to Your Charming Oasis at 2900 Oranole Rd, Orlando, FL 32810 This delightful 3-bedroom, 2-bathroom home offers the perfect blend of comfort, charm, and convenience. From the moment you step inside, you’ll appreciate the bright, airy ambiance, spacious living areas, and a private primary suite complete with its own en-suite bath. Culinary enthusiasts will love the cheerful kitchen, which

  Gretchen Carlson REAL BROKER, LLC

  2900 Oranole Rd, Orlando, FL 32810
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  /89

  $1,799,999

  • 6 Beds
  • 4 Baths
  • 3,853 Sq Ft

  1451 Lyndale Blvd, Winter Park, FL 32789

  Listed at APPRAISED VALUE **Luxurious Winter Park Estate with Detached TWO bedroom Guest House** RENOVATED POOL HOME with NO HOA! TWO Primary Bedrooms located on the main floor! Welcome to a world of unparalleled luxury and elegance in the heart of historic Winter Park, FL. This exquisitely renovated two-story pool home, set on a sprawling corner lot, offers a rare opportunity to experience the

  Christopher Soucy REALTY ONE GROUP MVP

  1451 Lyndale Blvd, Winter Park, FL 32789
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  /18

  $4,199,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,891 Sq Ft

  1417 Williams Dr, Winter Park, FL 32789

  Under Construction. Tucked away on a quiet cul-de-sac in the coveted Park Grove community, this home sits on an expansive 0.37-acre lot, just moments from the boutiques, dining, and charm of Park Avenue. The exterior makes a striking first impression with a refined architectural façade that feels both timeless and distinctive. Inside, a dramatic 20-foot foyer welcomes you with abundant natural

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1417 Williams Dr, Winter Park, FL 32789

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