Maitland, FL Homes

/41
$1,390,000
- 5 Beds
- 4.5 Baths
- 4,280 Sq Ft
1256 Wellington Terrace, Maitland, FL 32751

HARD TO FIND SKI LAKEFRONT! Classic traditional beauty – ready for a lucky buyer to make home. Stunning water & sunset views over Lake of the Woods from most living areas. Enter into the impressive foyer with curved stairway; light & bright large formal rooms with French doors to wrap around covered porch; Large open kitchen, wood cabinets, granite tops, stainless appliances and breakfast nook to

Lisa Gould KELLER WILLIAMS WINTER PARK

1256 Wellington Terrace, Maitland, FL 32751
/16
$2,113 per month
- 1 Bed
- 1 Bath
- 712 Sq Ft
- Condo for Rent
9301 Summit Centre Way Unit 1313, Orlando, FL 32810

Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $2526/mo12-Month+ Stay base rent: starts at $2113/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 1313, Orlando, FL 32810
/2
$507,200 Sold Dec 04, 2025

1550 Ridgewood Ave, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,760 Sq Ft
- Built 1989
Last Sold Summary
- 2% Below List Price
- $288/SF
- 46 Days On Market
Current Estimated Value $529,171

Last Listing Agent Justin Pekarek ORLANDO PROPERTY ADVISORS

1550 Ridgewood Ave, Maitland, FL 32751

/2
Est $280,753 Not Listed For Sale

1000 Winderley Place Unit 221, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,275 Sq Ft
- Built 1982
1000 Winderley Place Unit 221, Maitland, FL 32751

Last Sold Summary
- 9% Below List Price
- $242/SF
- 13 Days On Market
Last Sold Price $309,000

Last Listing Agent Jean Chalifour COLDWELL BANKER REALTY

/19
$650,000 Pending
- 3 Beds
- 2 Baths
- 2,044 Sq Ft
1000 Kewannee Trail, Maitland, FL 32751

Under contract-accepting backup offers. WELCOME TO YOUR DOMMERICH HOME - This tastefully updated Mid Century ranch is perfectly positioned on a gentle rise above the tree lined streets of Dommerich, offering both charm and modern functionality. As you enter the foyer, you are immediately welcomed by the clean lines and modern touches of the decor. The imported Italian tile and Terrazzo floors

David Teller ABSOLUTE REALTY GROUP, LLC

1000 Kewannee Trail, Maitland, FL 32751
/16
$2,113 per month
- 1 Bed
- 1 Bath
- 712 Sq Ft
- Condo for Rent
9301 Summit Centre Way Unit 2313, Orlando, FL 32810

Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $2597/mo12-Month+ Stay base rent: starts at $2113/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 2313, Orlando, FL 32810
/2
$579,000 Sold Oct 10, 2025

1434 Winston Rd, Maitland, FL 32751
- 4 Beds
- 2 Baths
- 2,312 Sq Ft
- Built 1971
Last Sold Summary
- $250/SF
- 16 Days On Market
Current Estimated Value $565,013

Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

1434 Winston Rd, Maitland, FL 32751

/2
Est $341,626 Not Listed For Sale

1000 S Orlando Ave Unit 2, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 952 Sq Ft
- Built 1964
1000 S Orlando Ave Unit 2, Maitland, FL 32751

Last Sold Summary
- 9% Below List Price
- $394/SF
- 25 Days On Market
Last Sold Price $375,000

Last Listing Agent Loralee Rider RIDER REALTY, LLC

/44
$529,500 Pending
- 4 Beds
- 2 Baths
- 1,824 Sq Ft
721 Gamewell Ave, Maitland, FL 32751

Welcome to one of Maitland’s most unique and captivating pool homes — perfectly positioned just steps from downtown Maitland and Lake Lily Park.This stunning 4-bedroom, 2-bath residence combines architectural character with everyday livability. Soaring vaulted ceilings and expansive windows flood the home with natural light, creating a sun-drenched family room that feels both grand and

Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

721 Gamewell Ave, Maitland, FL 32751
/17
$2,113 per month
- 1 Bed
- 1 Bath
- 712 Sq Ft
- Condo for Rent
9301 Summit Centre Way Unit 1223, Orlando, FL 32810

Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $2526/mo12-Month+ Stay base rent: starts at $2113/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 1223, Orlando, FL 32810
/2
$255,000 Sold Dec 08, 2025

240 Cherrywood Dr, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,161 Sq Ft
- Built 1959
Last Sold Summary
- 9% Below List Price
- $220/SF
- 6 Days On Market
Current Estimated Value $260,825

Last Listing Agent Martha Grasty EXP REALTY LLC

240 Cherrywood Dr, Maitland, FL 32751

/2
Est $177,139 Not Listed For Sale

222 Cherrywood Gardens Dr Unit 7, Maitland, FL 32751
- 2 Beds
- 1.5 Baths
- 953 Sq Ft
- Built 1974
222 Cherrywood Gardens Dr Unit 7, Maitland, FL 32751

Last Sold Summary
- 3% Below List Price
- $191/SF
- 48 Days On Market
Last Sold Price $182,100

Last Listing Agent Allison Day RE/MAX

/35
$419,900 Pending
- 4 Beds
- 2.5 Baths
- 2,473 Sq Ft
1404 Stratford Rd, Maitland, FL 32751

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Spacious one-story home featuring 4 bedrooms and 2.5 bathrooms with a functional, open layout. The kitchen offers a convenient breakfast bar overlooking the dining area. Step outside to enjoy the screened-in back porch and private in-ground pool, perfect for relaxing or hosting gatherings. The wood-fenced

Eva Hockenberry MAINSTAY BROKERAGE LLC

1404 Stratford Rd, Maitland, FL 32751
/16
$2,504 per month
- 2 Beds
- 2 Baths
- 1,115 Sq Ft
- Condo for Rent
9301 Summit Centre Way Unit 1318, Orlando, FL 32810

Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $2996/mo12-Month+ Stay base rent: starts at $2504/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 1318, Orlando, FL 32810
/2
$330,000 Sold Dec 30, 2025

735 Gamewell Ave, Maitland, FL 32751
- 2 Beds
- 1 Bath
- 938 Sq Ft
- Built 1952
Last Sold Summary
- $352/SF
- 2 Days On Market
Current Estimated Value $325,447

Last Listing Agent Heather Pryor KELLER WILLIAMS ADVANTAGE REALTY

735 Gamewell Ave, Maitland, FL 32751

/22
Est $255,802 Not Listed For Sale

1714 Gulfview Dr Unit 427-C, Maitland, FL 32751
- 3 Beds
- 3 Baths
- 1,328 Sq Ft
- Built 1981
1714 Gulfview Dr Unit 427-C, Maitland, FL 32751

Last Sold Summary
- 15% Below List Price
- $226/SF
- 1 Day On Market
Last Sold Price $300,000

Last Listing Agent Yien Yao KELLER WILLIAMS ADVANTAGE 2 REALTY

/32
$2,195,000
- 4 Beds
- 3.5 Baths
- 3,754 Sq Ft
1111 Audubon Way, Maitland, FL 32751

Welcome to a rare opportunity on the shores of Lake Sybelia, one of Maitland’s most desirable recreational lakes. This custom, one-owner home offers 3,754 square feet of thoughtfully designed living space where timeless craftsmanship meets peaceful waterfront living.A brick-paved horseshoe driveway and inviting front porch set the tone. Inside, rich wood floors, vaulted wood ceilings in the

Melissa Shipp KELLER WILLIAMS ADVANTAGE REALTY

1111 Audubon Way, Maitland, FL 32751
/19
$2,095 per month
- 2 Beds
- 2 Baths
- Condo for Rent
3016 Legacy Villas Dr, Maitland, FL 32751

Property Id: 1456532Spacious & QUIET 2/2 plus office with door, could be 3rd bedroom with 2 car garage available in Visconti; a nice resort style gated community with 2 large swimming pools, car washing station, fitness center, game room, tennis and basketball courts. Across the street from the Fire/Police station Close to everything, only minutes away from Altamonte Mall, WP

3016 Legacy Villas Dr, Maitland, FL 32751
/2
$385,000 Sold Feb 24, 2026

210 Magnolia Rd Unit 106, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,394 Sq Ft
- Built 1971
Last Sold Summary
- 4% Below List Price
- $276/SF
- 16 Days On Market
Current Estimated Value $322,298

Last Listing Agent Sue Gilman KELLER WILLIAMS WINTER PARK

210 Magnolia Rd Unit 106, Maitland, FL 32751

/2
Est $334,900 Not Listed For Sale

472 Citrus Ln, Maitland, FL 32751
- 3 Beds
- 2.5 Baths
- 1,665 Sq Ft
- Built 1983
472 Citrus Ln, Maitland, FL 32751

Last Sold Summary
- 6% Below List Price
- $213/SF
- 91 Days On Market
Last Sold Price $355,000

Last Listing Agent Mitch Mells Weichert Corporate

/31
$249,000
- 3 Beds
- 2 Baths
- 1,256 Sq Ft
602 Villa Cir Unit 543, Maitland, FL 32751

Experience the pinnacle of worry-free living in this stunningly renovated, single-story villa located in the highly desirable Park Lake community of Maitland. This home has been meticulously updated with a focus on efficiency and modern luxury, featuring brand-new energy-efficient sliding glass doors (2025), new Roof, new solid wood bedroom and closet doors, New plantation shutters (2024), new AC

Odel Ximinies COLDWELL BANKER REALTY

602 Villa Cir Unit 543, Maitland, FL 32751
/17
$2,113 per month
- 1 Bed
- 1 Bath
- 712 Sq Ft
- Condo for Rent
9301 Summit Centre Way Unit 4303, Orlando, FL 32810

Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $2526/mo12-Month+ Stay base rent: starts at $2113/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 4303, Orlando, FL 32810
/2
$555,000 Sold Oct 01, 2025

1771 Chinook Trail, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,704 Sq Ft
- Built 1959
Last Sold Summary
- 4% Below List Price
- $326/SF
- 20 Days On Market
Current Estimated Value $552,270

Last Listing Agent Hazel Sun RE/MAX 200 REALTY

1771 Chinook Trail, Maitland, FL 32751

/2
Est $268,832 Not Listed For Sale

854 Town Cir Unit 116, Maitland, FL 32751
- 3 Beds
- 2.5 Baths
- 1,565 Sq Ft
- Built 1974
854 Town Cir Unit 116, Maitland, FL 32751

Last Sold Summary
- 9% Below List Price
- $189/SF
- 18 Days On Market
Last Sold Price $296,000

Last Listing Agent Kim North COLDWELL BANKER STEVENS RE

/100
$1,349,000
- 4 Beds
- 5 Baths
- 4,149 Sq Ft
51 Oakleigh Ln, Maitland, FL 32751

WELCOME TO THIS FULLY RENOVATED LUXURY RESIDENCE IN THE HIGHLY DESIRABLE OAKLEIGH SUBDIVISION IN MAITLAND, offering OVER 4,149 SQ FT OF BEAUTIFULLY UPDATED LIVING SPACE on a 0.36-ACRE LOT WITH A PRIVATE POOL, designed for both elegance and everyday comfort. Originally built in 1972 and COMPLETELY MODERNIZED, this SINGLE-STORY ESTATE FEATURES 4 BEDROOMS AND 5 FULL BATHROOMS, including TWO

Ricardo Adames LA ROSA REALTY CW PROPERTIES L

51 Oakleigh Ln, Maitland, FL 32751
/20
$2,195 per month
- 2 Beds
- 1 Bath
- 1,146 Sq Ft
- House for Rent
1730 Ridgewood Ave, Maitland, FL 32751

Property Id: 1799893LOCATION, LOCATION, LOCATION! Fabulous cottage in the heart of Winter Park / Maitland. This charming 1,146sf, 2-bedroom, 1-bath home is just off N Park Ave, it's close to Orlando Ave, Whole Foods, Publix, and in walking distance to The Enzian. The home sits with an expansive back yard with beautiful mature trees and a barbeque patio. It includes a detached garage with

1730 Ridgewood Ave, Maitland, FL 32751
/2
$1,820,000 Sold Jun 07, 2025

251 W Trotters Dr, Maitland, FL 32751
- 4 Beds
- 2.5 Baths
- 3,524 Sq Ft
- Built 1964
Last Sold Summary
- 4% Below List Price
- $516/SF
- 8 Days On Market
Current Estimated Value $1,843,394

Last Listing Agent Audra Wilks PREMIER SOTHEBY'S INTL. REALTY

251 W Trotters Dr, Maitland, FL 32751

/2
Est $214,435 Not Listed For Sale

1501 Grove St Unit 560, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,087 Sq Ft
- Built 1979
1501 Grove St Unit 560, Maitland, FL 32751

Last Sold Summary
- 6% Below List Price
- $211/SF
- 57 Days On Market
Last Sold Price $229,000

Last Listing Agent Rebecca Hopson CHARLES RUTENBERG REALTY ORLANDO

/14
$120,000
- 1 Bed
- 1 Bath
- 550 Sq Ft
2517 Caper Ln Unit 205, Maitland, FL 32751

**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

MAYOLET BORNAS MAYOLET REALTY LLC

2517 Caper Ln Unit 205, Maitland, FL 32751
/17
$2,113 per month
- 1 Bed
- 1 Bath
- 712 Sq Ft
- Condo for Rent
9301 Summit Centre Way Unit 4307, Orlando, FL 32810

Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $2526/mo12-Month+ Stay base rent: starts at $2113/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 4307, Orlando, FL 32810
/2
$515,000 Sold Nov 07, 2025

2162 Lake Howell Preserve Ct, Maitland, FL 32751
- 3 Beds
- 3.5 Baths
- 2,188 Sq Ft
- Built 2021
Last Sold Summary
- 6% Below List Price
- $235/SF
- 27 Days On Market
Last Listing Agent Mark Raumaker SERHANT

2162 Lake Howell Preserve Ct, Maitland, FL 32751

/2
Est $213,035 Not Listed For Sale

1225 Lake Shadow Cir Unit 14202, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,111 Sq Ft
- Built 2000
1225 Lake Shadow Cir Unit 14202, Maitland, FL 32751

Last Sold Summary
- 9% Below List Price
- $212/SF
- 55 Days On Market
Last Sold Price $235,000

Last Listing Agent Kati Ettinger INNOVATIVE REALTY, LLC

/44
$615,000 Pending
- 4 Beds
- 2 Baths
- 2,400 Sq Ft
2462 Markingham Rd, Maitland, FL 32751

Under contract-accepting backup offers. Conveniently located in the established subdivision of English Estates, this updated and upgraded 4 bed, 2 Bath pool home is sure to please. From the moment you drive down the tree lined street you will sense the pride in this charming neighborhood. Come home and relax in the fully fenced in back yard that was transformed into a personal outdoor haven

Steven Kwong CHARLES RUTENBERG REALTY ORLANDO

2462 Markingham Rd, Maitland, FL 32751
/16
$2,504 per month
- 2 Beds
- 2 Baths
- 1,115 Sq Ft
- Condo for Rent
9301 Summit Centre Way Unit 2311, Orlando, FL 32810

Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $2922/mo12-Month+ Stay base rent: starts at $2504/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 2311, Orlando, FL 32810
/2
$335,000 Sold Oct 03, 2025

180 N Lakewood Cir, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,050 Sq Ft
- Built 1971
Last Sold Summary
- 22% Below List Price
- $319/SF
- 301 Days On Market
Current Estimated Value $319,461

Last Listing Agent Todd Norwood BESPOKE REAL ESTATE

180 N Lakewood Cir, Maitland, FL 32751

/40
Est $327,667 Not Listed For Sale

1010 Winderley Place Unit 131, Maitland, FL 32751
- 3 Beds
- 2.5 Baths
- 1,563 Sq Ft
- Built 1997
1010 Winderley Place Unit 131, Maitland, FL 32751

Last Sold Summary
- 8% Below List Price
- $227/SF
- 17 Days On Market
Last Sold Price $355,000

Last Listing Agent Jean Chalifour COLDWELL BANKER REALTY

/39
$546,900 Pending
- 3 Beds
- 2.5 Baths
- 1,575 Sq Ft
1531 Glastonberry Rd, Maitland, FL 32751

Under contract-accepting backup offers. ***UNDER CONTRACT - ACCEPTING BACKUP OFFERS*** Welcome to this stunning 3-bedroom home offering modern upgrades, thoughtful design, and exceptional indoor-outdoor living.Extensively remodeled in 2021, the interior of this home was thoughtfully updated to create a modern and inviting space. The highly desirable open floor plan seamlessly connects the kitchen

Brandon Frank YOUNG REAL ESTATE

1531 Glastonberry Rd, Maitland, FL 32751
/16
$2,699 per month
- 3 Beds
- 2 Baths
- 1,743 Sq Ft
- House for Rent
720 Bucher Rd, Maitland, FL 32751

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2843.90. That covers your base rent, $2699.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

720 Bucher Rd, Maitland, FL 32751
/2
$1,350,000 Sold Oct 01, 2025

2047 Howell Branch Rd, Maitland, FL 32751
- 4 Beds
- 2 Baths
- 2,960 Sq Ft
- Built 1986
Last Sold Summary
- 10% Below List Price
- $456/SF
- 28 Days On Market
Current Estimated Value $1,309,942

Last Listing Agent Shelby Smith KELLY PRICE & COMPANY LLC

2047 Howell Branch Rd, Maitland, FL 32751

/22
Est $189,518 Not Listed For Sale

216 Cherrywood Gardens Dr Unit 216, Maitland, FL 32751
- 2 Beds
- 1.5 Baths
- 953 Sq Ft
- Built 1974
216 Cherrywood Gardens Dr Unit 216, Maitland, FL 32751

Last Sold Summary
- 16% Below List Price
- $236/SF
- 3 Days On Market
Last Sold Price $225,000

Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

Showing Results 161 - 200, Page 5 of 18

Florida Orange County Maitland

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