Maitland, FL Homes

/34
Est $419,606

Not Listed For Sale

1100 S Orlando Ave Unit 604, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,285 Sq Ft
- Built 1973
1100 S Orlando Ave Unit 604, Maitland, FL 32751

Last Sold Summary
- 11 Days On Market

/28
$500,000

$50K PRICE DROP
- 4 Beds
- 3 Baths
- 2,748 Sq Ft
140 E Faith Terrace, Maitland, FL 32751

One or more photo(s) has been virtually staged. NEW ROOF 2022 - NEW AC 2022 - NEW ELECTRICAL PANELS 2022 - REPLUMB 2022 - NEW SEPTIC 2023 - Seperate detached GUEST HOUSE offering built-in monthly income potential. Previously rented under market value at $900/month, the guesthouse is currently vacant and ready for a new tenant, a private space for adult children, or a comfortable in-law suite.

Gregory Roberts LPT REALTY LLC

140 E Faith Terrace, Maitland, FL 32751
/2
$250,000

Sold Aug 22, 2025

20 People St, Maitland, FL 32751
- Land
- 25,264 Sq Ft
- $431,034 per Acre
Last Sold Summary
- 10 Days On Market
Current Estimated Value $248,496

Last Listing Agent Julia Meffen FLORIDA HOMES & LOANS INC.

20 People St, Maitland, FL 32751

/2
Est $343,133

Not Listed For Sale

1000 S Orlando Ave Unit A24, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 952 Sq Ft
- Built 1964
1000 S Orlando Ave Unit A24, Maitland, FL 32751

Last Sold Summary
- 28 Days On Market

/34
$490,000

Pending
- 3 Beds
- 2.5 Baths
- 1,870 Sq Ft
1106 Charming St, Maitland, FL 32751

Under contract-accepting backup offers. Welcome to this beautifully maintained lakefront townhome in a highly desirable gated community in Maitland with almost 1900 square feet of thoughtfully designed living space. This 3-bedroom, 2.5-bath residence combines comfort, functionality, and picturesque lake views. Enjoy serene views of Lake Charity from the charming front porch, formal dining room,

Donna Bryant COLDWELL BANKER REALTY

1106 Charming St, Maitland, FL 32751
/2
$235,000

Sold Aug 14, 2025

1140 S Orlando Ave Unit K15, Maitland, FL 32751
- 2 Beds
- 1.5 Baths
- 816 Sq Ft
- Built 1966
Last Sold Summary
- 24% Below List Price
- $288/SF
- 194 Days On Market
Current Estimated Value $239,998

Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

1140 S Orlando Ave Unit K15, Maitland, FL 32751

/2
Est $488,346

Not Listed For Sale

202 Quayside Cir Unit 201, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,203 Sq Ft
- Built 1984
202 Quayside Cir Unit 201, Maitland, FL 32751

Last Sold Summary
- 64 Days On Market

/33
$415,000
- 4 Beds
- 2 Baths
- 1,538 Sq Ft
1327 Chipola Trail, Maitland, FL 32751

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

Abbas Sultanali ALPHA EQUITY REALTY & MANAGEMENT INC

1327 Chipola Trail, Maitland, FL 32751
/2
$379,000

Sold Dec 29, 2025

518 Oak Ln, Maitland, FL 32751
- 3 Beds
- 3 Baths
- 1,999 Sq Ft
- Built 1957
Last Sold Summary
- 10% Below List Price
- $190/SF
- 21 Days On Market
Current Estimated Value $391,922

Last Listing Agent Sonia Dublis COLDWELL BANKER REALTY

518 Oak Ln, Maitland, FL 32751

/39
Est $441,174

Not Listed For Sale

1140 S Orlando Ave Unit K9, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,246 Sq Ft
- Built 1966
1140 S Orlando Ave Unit K9, Maitland, FL 32751

Last Sold Summary
- 0 Days On Market

/39
$659,900
- 3 Beds
- 2.5 Baths
- 2,110 Sq Ft
1404 Caring Ct, Maitland, FL 32751

"RARE OPPORTUNITY" MOVE-IN READY 3-BED, 2.5-BATH SINGLE FAMILY HOME IN THE "EXCLUSIVE GATED COMMUNITY OF ENCLAVE AT MAITLAND", FL 32751. Nestled within the highly sought-after & gated community of Enclave at Maitland, Single Family Homes rarely come on the market and this home offers a Luxury Interior Footprint that's a perfect balance of privacy, elegance, and convenience. Fully updated & loaded

Joel Bornstein ROCK SPRINGS REALTY, LLC

1404 Caring Ct, Maitland, FL 32751
/2
$678,500

Sold Jul 18, 2025

1921 Geronimo Trail, Maitland, FL 32751
- 4 Beds
- 3 Baths
- 2,167 Sq Ft
- Built 1970
Last Sold Summary
- $313/SF
- 4 Days On Market
Current Estimated Value $696,750

Last Listing Agent Kayla Mcclean COMPASS FLORIDA LLC

1921 Geronimo Trail, Maitland, FL 32751

/50
Est $340,487

Not Listed For Sale

1000 S Orlando Ave Unit A26, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 952 Sq Ft
- Built 1964
1000 S Orlando Ave Unit A26, Maitland, FL 32751

Last Sold Summary
- 64 Days On Market

/28
$499,900

$10K PRICE DROP
- 3 Beds
- 2 Baths
- 1,683 Sq Ft
370 Sultana Ln, Maitland, FL 32751

PRICE IMPROVEMENT: Welcome to 370 Sultana Lane, a fully renovated 3-bedroom, 2-bathroom home located in the highly desirable Druid Hills community of Maitland. With over $60,000 in thoughtful upgrades and paid off solar, this move-in-ready residence offers modern comfort without the hassle of future projects. Step inside to a fully reimagined open floor plan designed for both everyday living and

Melissa Osborne EQUITYPRO LLC

370 Sultana Ln, Maitland, FL 32751
/2
$340,000

Sold Jan 16, 2026

2352 Sierra Ln, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,343 Sq Ft
- Built 1984
Last Sold Summary
- $253/SF
- 6 Days On Market
Current Estimated Value $332,815

Last Listing Agent Shirley Welch BHHS FLORIDA REALTY

2352 Sierra Ln, Maitland, FL 32751

/31
Est $377,401

Not Listed For Sale

1000 S Orlando Ave Unit A4, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 952 Sq Ft
- Built 1964
1000 S Orlando Ave Unit A4, Maitland, FL 32751

Last Sold Summary
- 19 Days On Market

/47
$749,900

Open Sat 1PM - 4PM $75K PRICE DROP
- 3 Beds
- 2 Baths
- 2,375 Sq Ft
2040 Geronimo Trail, Maitland, FL 32751

Virtually Staged. Set on one of the most sought-after streets in Dommerich, this completely renovated home combines the solid construction of a 1963 block home with thoughtful modern updates throughout. From the moment you arrive, the circular driveway, classic brick accents, and welcoming front porch set the tone. Inside, a bright foyer opens to beautiful solid maple wood floors and a light,

Maria Van Warner FANNIE HILLMAN & ASSOCIATES

2040 Geronimo Trail, Maitland, FL 32751
/2
$410,000

Sold Sep 05, 2025

2132 Tortoise Shell Dr, Maitland, FL 32751
- 4 Beds
- 2 Baths
- 1,809 Sq Ft
- Built 1996
Last Sold Summary
- 4% Below List Price
- $227/SF
- 15 Days On Market
Current Estimated Value $414,289

Last Listing Agent Gale Milgrim KELLER WILLIAMS WINTER PARK

2132 Tortoise Shell Dr, Maitland, FL 32751

/34
Est $255,528

Not Listed For Sale

1140 S Orlando Ave Unit H12, Maitland, FL 32751
- 2 Beds
- 1 Bath
- 816 Sq Ft
- Built 1966
1140 S Orlando Ave Unit H12, Maitland, FL 32751

Last Sold Summary
- 4 Days On Market

/39
$619,000

$60K PRICE DROP
- 3 Beds
- 2 Baths
- 1,922 Sq Ft
1750 Pocahontas Path, Maitland, FL 32751

Set along a quiet, tree-lined street in Maitland, this 3 bedroom, 2 bathroom home with 1,922 square feet captures the essence of mid-century modern design with a fresh, updated edge. Clean lines, open flow, and a strong connection to the outdoors define the home from the moment you step inside. Major updates include the kitchen in 2019, bathrooms in 2021, Roof 2022, and HVAC in 2024. The living

Brian Rotenberger COMPASS FLORIDA LLC

1750 Pocahontas Path, Maitland, FL 32751
/2
$1,035,000

Sold Sep 30, 2025

904 Brightwater Cir, Maitland, FL 32751
- 4 Beds
- 3.5 Baths
- 3,099 Sq Ft
- Built 1997
Last Sold Summary
- 1% Below List Price
- $334/SF
- 9 Days On Market
Current Estimated Value $1,038,335

Last Listing Agent Erin Baker FANNIE HILLMAN & ASSOCIATES

904 Brightwater Cir, Maitland, FL 32751

/34
Est $193,778

Not Listed For Sale

1140 S Orlando Ave Unit E3, Maitland, FL 32751
- 1 Bed
- 1 Bath
- 612 Sq Ft
- Built 1971
1140 S Orlando Ave Unit E3, Maitland, FL 32751

Last Sold Summary
- 23 Days On Market

/25
$199,000

$11K PRICE DROP
- 2 Beds
- 1 Bath
- 898 Sq Ft
1375 Lake Shadow Cir Unit 11103, Maitland, FL 32751

Stunning fully renovated 2-bedroom, 1-bath condo featuring a complete top-to-bottom remodel completed in 2026, located in the highly desirable gated Visconti West community in Maitland. This move-in ready unit features luxury vinyl plank flooring throughout, a beautifully updated kitchen with modern soft-close cabinetry, sleek finishes, and stainless steel appliances, as well as a bright

Margo Ford M2M REALTY

1375 Lake Shadow Cir Unit 11103, Maitland, FL 32751
/2
$398,400

Sold May 21, 2026

2113 Falkner Rd, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,708 Sq Ft
- Built 1998
Last Sold Summary
- $233/SF
- 5 Days On Market
Current Estimated Value $397,208

Last Listing Agent Heather Travis LOCAL LIVING REALTY GROUP

2113 Falkner Rd, Maitland, FL 32751

/42
Est $227,135

Not Listed For Sale

1140 S Orlando Ave Unit A14, Maitland, FL 32751
- 2 Beds
- 1 Bath
- 816 Sq Ft
- Built 1964
1140 S Orlando Ave Unit A14, Maitland, FL 32751

Last Sold Summary
- 139 Days On Market

/45
$355,000
- 4 Beds
- 2 Baths
- 1,707 Sq Ft
2401 Legacy Lake Dr Unit 2401, Maitland, FL 32751

All roads lead to Visconti East! Located in Maitland, bordering nearby scenic Winter Park (Park Ave./ Rollins College) this distinctive 3 story, 4 Bed/2.5 Bath townhome is situated directly off of I-4 and SR414, within 10 minutes to Downtown Orlando, Park Avenue, and close access to SR429, Winter Garden, and North Orlando. This home offers a one-of-a-kind floor plan with the entry foyer, hall

Trace Christian, III COLDWELL BANKER REALTY

2401 Legacy Lake Dr Unit 2401, Maitland, FL 32751
/2
$321,500

Sold Dec 19, 2025

214 Cherrywood Dr, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,178 Sq Ft
- Built 1958
Last Sold Summary
- 16% Below List Price
- $273/SF
- 288 Days On Market
Current Estimated Value $321,118

Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

214 Cherrywood Dr, Maitland, FL 32751

/2
Est $316,303

Not Listed For Sale

210 Magnolia Rd Unit 110, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
- Built 1971
210 Magnolia Rd Unit 110, Maitland, FL 32751

Last Sold Summary
- 9 Days On Market

/39
$645,000

$25K PRICE DROP
- 3 Beds
- 2 Baths
- 2,214 Sq Ft
910 Gamewell Ave, Maitland, FL 32751

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

Sarah Tomlinson COMPASS FLORIDA LLC

910 Gamewell Ave, Maitland, FL 32751
/2
$385,000

Sold Mar 31, 2026

314 Banyan Dr, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,234 Sq Ft
- Built 1972
Last Sold Summary
- 4% Below List Price
- $312/SF
- 122 Days On Market
Current Estimated Value $379,363

Last Listing Agent Ivanhoe Alvarez LOKATION

314 Banyan Dr, Maitland, FL 32751

/8
Est $256,041

Not Listed For Sale

1000 Winderley Place Unit 146, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
- Built 1985
1000 Winderley Place Unit 146, Maitland, FL 32751

Last Sold Summary
- 27 Days On Market

/24
$799,000

$70K PRICE DROP
- 4 Beds
- 2 Baths
- 2,681 Sq Ft
320 White Oak Cir, Maitland, FL 32751

ENTERTAINING MAITLAND GROVE POOL HOME. Step inside to discover oversized rooms, including a spacious great room overlooking the covered lanai and swimming pool in a private setting perfect for gatherings. Back yard includes a vinyl privacy fence, Pool resurfaced with Pebble Tec. Patio and pool decking have pavers with plenty of room for extra lounging. Lots of Room for everyone, including lIving

Susan Filebark OVERSTREET REAL ESTATE INC

320 White Oak Cir, Maitland, FL 32751
/2
$515,000

Sold Oct 11, 2025

1411 Glastonberry Rd, Maitland, FL 32751
- 5 Beds
- 2 Baths
- 2,082 Sq Ft
- Built 1965
Last Sold Summary
- 4% Below List Price
- $247/SF
- 17 Days On Market
Current Estimated Value $511,985

Last Listing Agent Patrick Urbainczyk P.A. KELLER WILLIAMS HERITAGE REALTY

1411 Glastonberry Rd, Maitland, FL 32751

/2
Est $304,212

Not Listed For Sale

1000 Winderley Place Unit 240, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,538 Sq Ft
- Built 1982
1000 Winderley Place Unit 240, Maitland, FL 32751

/97
$850,000
- 4 Beds
- 2 Baths
- 1,870 Sq Ft
109 Kyle Dr, Maitland, FL 32751

A tropical retreat in Minnehaha Shores with deeded lake access to the Winter Park Chain of Lakes. Tree-lined streets welcome you to this beautifully reimagined four-bedroom, two-bath split-plan home with coastal influences throughout. Formal living, dining and family spaces blend seamlessly together, creating great flexibility in layout. French doors line the back of the home and open to the

Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

109 Kyle Dr, Maitland, FL 32751
/2
$700,000

Sold Mar 27, 2026

814 N Thistle Ln, Maitland, FL 32751
- 4 Beds
- 2 Baths
- 2,136 Sq Ft
- Built 1960
Last Sold Summary
- $328/SF
- 2 Days On Market
Current Estimated Value $696,472

Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

814 N Thistle Ln, Maitland, FL 32751

/2
Est $208,107

Not Listed For Sale

1100 Lake Shadow Cir Unit 2305, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,048 Sq Ft
- Built 2000
1100 Lake Shadow Cir Unit 2305, Maitland, FL 32751

Last Sold Summary
- 39 Days On Market

/43
$379,000

Pending
- 3 Beds
- 2.5 Baths
- 1,674 Sq Ft
1393 Benevolent St, Maitland, FL 32751

This beautiful Maitland Florida town home feels like living in a gated resort! 3 bedrooms, 2 1/2 baths, plus garage and loaded with upgrades including hardwood floors on both levels, crown molding, tall wood cabinets, stone counters and so much more. Welcoming entry foyer with half bath, kitchen with island sink, large breakfast bar, stainless appliances, granite counters and custom backsplash.

Daniel Rencher RENCHER REALTY GROUP

1393 Benevolent St, Maitland, FL 32751
/2
$359,706

Sold Feb 10, 2026

2464 Derbyshire Rd, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,860 Sq Ft
- Built 1963
Last Sold Summary
- 16% Below List Price
- $193/SF
- 68 Days On Market
Current Estimated Value $526,760

Last Listing Agent Jennifer Vilayvong VYLLA HOME

2464 Derbyshire Rd, Maitland, FL 32751

/29
Est $213,614

Not Listed For Sale

1408 Lake Shadow Cir Unit 1301, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,111 Sq Ft
- Built 2000
1408 Lake Shadow Cir Unit 1301, Maitland, FL 32751

Last Sold Summary
- 27 Days On Market

Showing Results 361 - 400, Page 10 of 18

Florida Orange County Maitland

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