Maitland, FL Homes

/29
$449,000

Pending
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
775 Woodside Rd, Maitland, FL 32751

Under contract-accepting backup offers. 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

Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

775 Woodside Rd, Maitland, FL 32751
/20
$2,345 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 $2348/mo12-Month+ Stay base rent: starts at $2345/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 1318, Orlando, FL 32810
/2
$1,090,000

Sold Jun 11, 2026

1256 Wellington Terrace, Maitland, FL 32751
- 5 Beds
- 4.5 Baths
- 4,280 Sq Ft
- Built 1987
Last Sold Summary
- 25% Below List Price
- $255/SF
- 94 Days On Market
Current Estimated Value $1,366,515

Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

1256 Wellington Terrace, Maitland, FL 32751

/46
Est $279,377

Not Listed For Sale

1000 Winderley Place Unit 144, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,275 Sq Ft
- Built 1982
1000 Winderley Place Unit 144, Maitland, FL 32751

Last Sold Summary
- 4 Days On Market

/32
$300,000

Open Sat 11AM - 2PM
- 2 Beds
- 2 Baths
- 1,275 Sq Ft
1000 Winderley Place Unit 141, Maitland, FL 32751

Updated GROUND-FLOOR condo in the secluded gated community of Sun Bay Club in Maitland, Florida overlooking Lake Destiny. Many units sit on lake fed ponds with fountains which offer a tranquil and peaceful atmosphere. Enjoy Florida life with a tennis court, a beautiful LAKE FRONT POOL, and LAKE ACCESS for residents to use boats and jet skis. The open-concept layout makes this 2 bedroom/2 bath

Cece Wong EXP REALTY LLC

1000 Winderley Place Unit 141, Maitland, FL 32751
/20
$1,956 Per Month
- 1 Bed
- 1 Bath
- 805 Sq Ft
- Condo for Rent
9301 Summit Centre Way Unit 3225, 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 $1956/mo12-Month+ Stay base rent: starts at $1956/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 3225, Orlando, FL 32810
/2
$970,000

Sold Sep 04, 2025

2031 Chippewa Trail, Maitland, FL 32751
- 4 Beds
- 3 Baths
- 2,385 Sq Ft
- Built 1961
Last Sold Summary
- $407/SF
Current Estimated Value $955,002

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

2031 Chippewa Trail, Maitland, FL 32751

/11
Est $110,418

Not Listed For Sale

2422 Branch Way Unit 200, Maitland, FL 32751
- 1 Bed
- 1 Bath
- 550 Sq Ft
- Built 1973
2422 Branch Way Unit 200, Maitland, FL 32751

Last Sold Summary
- 19 Days On Market

/38
$1,135,000

$105K PRICE DROP
- 4 Beds
- 4 Baths
- 4,149 Sq Ft
51 Oakleigh Ln, Maitland, FL 32751

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.

Karen Albright OPENDOOR BROKERAGE LLC

51 Oakleigh Ln, Maitland, FL 32751
/19
$2,195 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
$647,000

Sold Apr 15, 2026

1000 Kewannee Trail, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 2,044 Sq Ft
- Built 1963
Last Sold Summary
- $317/SF
- 3 Days On Market
Current Estimated Value $638,649

Last Listing Agent David Teller ABSOLUTE REALTY GROUP, LLC

1000 Kewannee Trail, Maitland, FL 32751

/13
Est $155,682

Not Listed For Sale

1275 Lake Shadow Cir Unit 13208, Maitland, FL 32751
- 1 Bed
- 1 Bath
- 672 Sq Ft
- Built 2000
1275 Lake Shadow Cir Unit 13208, Maitland, FL 32751

Last Sold Summary
- 136 Days On Market

/62
$849,000

Pending
- 4 Beds
- 3 Baths
- 2,610 Sq Ft
457 Forestwood Ln, Maitland, FL 32751

Under contract-accepting backup offers. From the moment you step inside, you’re welcomed by a stunning double-sided fireplace and a sought-after conversation pit — the perfect setting to unwind with your favorite vinyl record, a glass of wine, and great company.Beyond the fireplace, the home opens into an expansive open-concept living space designed for both everyday comfort and effortless

Anthony DiNova UNITED REAL ESTATE PREFERRED

457 Forestwood Ln, Maitland, FL 32751
/20
$1,956 Per Month
- 1 Bed
- 1 Bath
- 712 Sq Ft
- Condo for Rent
9301 Summit Centre Way Unit 1103, 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 $1956/mo12-Month+ Stay base rent: starts at $1956/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 1103, Orlando, FL 32810
/2
$330,000

Sold Jun 18, 2026

361 Hickory Dr, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,407 Sq Ft
- Built 1959
Last Sold Summary
- 11% Below List Price
- $235/SF
- 28 Days On Market
Current Estimated Value $352,912

Last Listing Agent Emma Nelson KELLER WILLIAMS REALTY AT THE PARKS

361 Hickory Dr, Maitland, FL 32751

/42
Est $201,086

Not Listed For Sale

1225 Lake Shadow Cir Unit 14203, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,048 Sq Ft
- Built 2000
1225 Lake Shadow Cir Unit 14203, Maitland, FL 32751

Last Sold Summary
- 21 Days On Market

/70
$2,395,000
- 5 Beds
- 3 Baths
- 3,456 Sq Ft
530 Lake Catherine Dr, Maitland, FL 32751

An incredible opportunity in one of Maitland’s exclusive communities offers stunning lakefront views of Lake Catherine and Lake Eulalia. With one of only three private docks on Lake Catherine, this is a rare and special property. A charming brick street winds along the lake and leads to this timeless residence, uniquely positioned with frontage on two lakes. This elegant two-story home features

Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

530 Lake Catherine Dr, Maitland, FL 32751
/20
$1,892 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 $1892/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 4303, Orlando, FL 32810
/2
$230,000

Sold Nov 14, 2025

1825 Shadow View Cir, Maitland, FL 32751
- 3 Beds
- 2.5 Baths
- 1,583 Sq Ft
- Built 2000
Last Sold Summary
- 8% Below List Price
- $145/SF
- 110 Days On Market
Last Listing Agent Chuck Lemire PLATINUM REAL ESTATE

1825 Shadow View Cir, Maitland, FL 32751

/12
Not Listed For Sale

1400 Lake Shadow Cir Unit 10204, Maitland, FL 32751
- 1 Bed
- 1 Bath
- 672 Sq Ft
- Built 2000
1400 Lake Shadow Cir Unit 10204, Maitland, FL 32751

Last Sold Summary
- 5 Days On Market

/27
$250,000
- 2 Beds
- 2 Baths
- 1,111 Sq Ft
1150 Lake Shadow Cir Unit 3307, Maitland, FL 32751

Welcome to Visconti, one of Central Florida's most sought-after gated communities. This stunning 3rd floor unit offers the privacy and natural light that only an end unit can deliver, w/ soaring high ceilings that elevate every room. Step out onto your private screened balcony and enjoy the fresh air in true Florida style. This 2-bed, 2-bath residence spans over 1,050 square feet and features

Donovan Armas Atlantic Florida Properties Inc

1150 Lake Shadow Cir Unit 3307, Maitland, FL 32751
/5
$1,050 Per Month
- 1 Bed
- 1 Bath
- 550 Sq Ft
- Condo for Rent
2422 Branch Way Unit 104, Maitland, FL 32751

Property Id: 2587286Cozy 1 bedroom 1 bath 1st floor unit. Excellent location on Howell Branch near 436. Unit features new flooring, spacious closet, and a pool view.

2422 Branch Way Unit 104, Maitland, FL 32751
/2
$529,500

Sold Mar 24, 2026

721 Gamewell Ave, Maitland, FL 32751
- 4 Beds
- 2 Baths
- 1,824 Sq Ft
- Built 1976
Last Sold Summary
- $290/SF
- 4 Days On Market
Current Estimated Value $524,531

Last Listing Agent Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

721 Gamewell Ave, Maitland, FL 32751

/26
Not Listed For Sale

1275 Lake Shadow Cir Unit 13305, Maitland, FL 32751
- 1 Bed
- 1 Bath
- 672 Sq Ft
- Built 2000
1275 Lake Shadow Cir Unit 13305, Maitland, FL 32751

/60
$1,100,000
- 5 Beds
- 4 Baths
- 3,270 Sq Ft
987 Brightwater Cir, Maitland, FL 32751

Your dream home awaits. Welcome to this exquisitely Renovated 4/4 PLUS OFFICE PLUS BONUS ROOM POOL HOME. Located in the gorgeous guard gated enclave of Maitland Club. From the moment you enter, soaring ceilings and an elegant 3-way split floor plan create a sense of openness and refined comfort. At the heart of the home lies a beautiful updated kitchen, complete with a spacious center island,

Gale Milgrim KELLER WILLIAMS WINTER PARK

987 Brightwater Cir, Maitland, FL 32751
/20
$1,956 Per Month
- 1 Bed
- 1 Bath
- 712 Sq Ft
- Condo for Rent
9301 Summit Centre Way Unit 1110, 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 $1956/mo12-Month+ Stay base rent: starts at $1956/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 1110, Orlando, FL 32810
/2
$235,000

Sold Jan 29, 2026

613 Orange Tree Ct Unit 507, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,256 Sq Ft
- Built 1974
Last Sold Summary
- 3% Below List Price
- $187/SF
- 10 Days On Market
Current Estimated Value $234,369

Last Listing Agent Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

613 Orange Tree Ct Unit 507, Maitland, FL 32751

/2
Est $266,326

Not Listed For Sale

1000 Winderley Place Unit 237, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,164 Sq Ft
- Built 1982
1000 Winderley Place Unit 237, Maitland, FL 32751

Last Sold Summary
- 24 Days On Market

/44
$1,386,000

Open Sun 1PM - 3PM
- 4 Beds
- 3 Baths
- 2,473 Sq Ft
1615 King Arthur Cir, Maitland, FL 32751

Beautifully updated pool home in the sought-after King's Row, Maitland community. This home blends timeless character with modern finishes. The corner lot residence features a three wide driveway, freshly updated landscaping and a commercial grade in ground basketball goal. Exterior paint (2026) creates warm curb appeal. Inside, new wood floors throughout lead to an open living space anchored by

Dan Haber CORCORAN PREMIER REALTY

1615 King Arthur Cir, Maitland, FL 32751
/9
$795 Per Month
- 1 Bed
- 1 Bath
- House for Rent
312 Orange St, Maitland, FL 32751

Property Id: 1784522ROOM RENTAL WITH ALL UTILIES INCLUDES SHARED SPACE

312 Orange St, Maitland, FL 32751
/2
$324,000

Sold Jun 18, 2026

1000 S Orlando Ave Unit B25, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 952 Sq Ft
- Built 1964
Last Sold Summary
- 3% Below List Price
- $340/SF
- 59 Days On Market
Current Estimated Value $331,589

Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

1000 S Orlando Ave Unit B25, Maitland, FL 32751

/2
Not Listed For Sale

1000 S Orlando Ave Unit 4, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 952 Sq Ft
- Built 1964
1000 S Orlando Ave Unit 4, Maitland, FL 32751

Last Sold Summary
- 43 Days On Market

/40
$215,000
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
1927 Legacy Cove Dr, Maitland, FL 32751

Virtually Staged. Resort-style amenities, low-maintenance living at a reasonable price, and a move-in ready home come together at 1927 Legacy Cove in beautiful Maitland. As you approach this GATED COMMUNITY, you will feel at ease with the added layer of security. Parking at the condo, you will see an extremely rare feature - an ATTACHED 2 CAR GARAGE! Inside, your eyes will be immediately drawn to

Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

1927 Legacy Cove Dr, Maitland, FL 32751
/20
$1,956 Per Month
- 1 Bed
- 1 Bath
- 790 Sq Ft
- Condo for Rent
9301 Summit Centre Way Unit 2316, 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 $1956/mo12-Month+ Stay base rent: starts at $1956/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 2316, Orlando, FL 32810
/2
$150,000

Sold Jul 31, 2025

539 Clark St, Maitland, FL 32751
- 3 Beds
- 1 Bath
- 936 Sq Ft
- Built 1951
Last Sold Summary
- 25% Below List Price
- $160/SF
- 70 Days On Market
Current Estimated Value $154,636

Last Listing Agent Alvin Moore MOREHOUSE REALTY INC

539 Clark St, Maitland, FL 32751

/2
Est $391,806

Not Listed For Sale

1000 Winderley Place Unit 152, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,970 Sq Ft
- Built 1985
1000 Winderley Place Unit 152, Maitland, FL 32751

Last Sold Summary
- 2 Days On Market

/32
$1,825,000

$370K PRICE DROP
- 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 that has been well-maintained with potential for cosmetic enhancements. A brick-paved horseshoe driveway and inviting front porch set the tone. Inside, rich wood floors, vaulted wood ceilings in

Melissa Shipp KELLER WILLIAMS ADVANTAGE REALTY

1111 Audubon Way, Maitland, FL 32751
/20
$2,350 Per Month
- 2 Beds
- 2 Baths
- 1,115 Sq Ft
- Condo for Rent
9301 Summit Centre Way Unit 2130, 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 $2353/mo12-Month+ Stay base rent: starts at $2350/moLanding's apartments at The Tiffany at

9301 Summit Centre Way Unit 2130, Orlando, FL 32810
/2
$270,000

Sold Jul 17, 2025

531 Wigman Dr, Maitland, FL 32751
- 4 Beds
- 1.5 Baths
- 1,301 Sq Ft
- Built 1965
Last Sold Summary
- 8% Below List Price
- $208/SF
- 9 Days On Market
Current Estimated Value $276,426

Last Listing Agent Anthony Figueroa LLC OUTLET REALTY

531 Wigman Dr, Maitland, FL 32751

/2
Est $230,975

Not Listed For Sale

808 Park Lake Cir Unit 5, Maitland, FL 32751
- 2 Beds
- 1.5 Baths
- 1,432 Sq Ft
- Built 1972
808 Park Lake Cir Unit 5, Maitland, FL 32751

Last Sold Summary
- 162 Days On Market

Showing Results 81 - 120, Page 3 of 18

Florida Orange County Maitland

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