Maitland, FL Homes

/30
$395,000
- 2 Beds
- 2 Baths
- 816 Sq Ft
1140 S Orlando Ave Unit F1, Maitland, FL 32751

This condo was completely renovated in 2023 and is located in one of the best spots within the complex. Positioned directly on the Winter Park chain of lakes, it offers excellent access to everything Winter Park and Maitland have to offer. Residents enjoy being within walking distance to a variety of restaurants and shopping, creating an ideal blend of convenience and lifestyle. This unique

Nickolas McKee KELLER WILLIAMS WINTER PARK

1140 S Orlando Ave Unit F1, Maitland, FL 32751
/2
$525,000 Sold Sep 18, 2025

503 Lake Shore Dr, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 2,054 Sq Ft
- Built 1959
Last Sold Summary
- $256/SF
- 17 Days On Market
Current Estimated Value $507,154

Last Listing Agent Tanya McDonnell RE/MAX TOWN & COUNTRY REALTY

503 Lake Shore Dr, Maitland, FL 32751

/59
Not Listed For Sale

1140 S Orlando Ave Unit E14, Maitland, FL 32751
- 2 Beds
- 1 Bath
- 816 Sq Ft
- Built 1971
1140 S Orlando Ave Unit E14, Maitland, FL 32751

Last Sold Summary
- 12% Above List Price
- $270/SF
- 59 Days On Market
Last Sold Price $220,000

Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

/29
$158,000
- 1 Bed
- 1 Bath
- 672 Sq Ft
1400 Lake Shadow Cir Unit 10104, Maitland, FL 32751

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to Visconti, a ~ GATED ~ WATERFRONT COMMUNITY ~ in the heart of Maitland where convenience and lifestyle come together. There is NOTHING you have to do this unit!! This well maintained, FIRST FLOOR, 1 bedroom, 1 bath condo is MOVE-IN READY and positioned with peaceful LAKE AND CONSERVATION

Jennifer Wemert WEMERT GROUP REALTY LLC

1400 Lake Shadow Cir Unit 10104, Maitland, FL 32751
/2
$251,500 Sold Oct 28, 2025

1140 S Orlando Ave Unit F9, Maitland, FL 32751
- 2 Beds
- 1.5 Baths
- 816 Sq Ft
- Built 1969
Last Sold Summary
- 1% Above List Price
- $308/SF
- 2 Days On Market
Last Listing Agent Allie George CORCORAN PREMIER REALTY

1140 S Orlando Ave Unit F9, Maitland, FL 32751

/2
Not Listed For Sale

1140 S Orlando Ave Unit B8, Maitland, FL 32751
- 2 Beds
- 1.5 Baths
- 816 Sq Ft
- Built 1964
1140 S Orlando Ave Unit B8, Maitland, FL 32751

Last Sold Summary
- $306/SF
- 22 Days On Market
Last Sold Price $250,000

Last Listing Agent Vince Indiveri LIVE FLORIDA NOW LLC

/21
$869,000 Open Sat 1PM - 3PM
- 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 May 22, 2025

1913 South Blvd, Maitland, FL 32751
- 4 Beds
- 3 Baths
- 2,416 Sq Ft
- Built 1969
Last Sold Summary
- 12% Below List Price
- $213/SF
- 243 Days On Market
Current Estimated Value $510,508

Last Listing Agent Juan Rijos LA ROSA REALTY ORLANDO LLC

1913 South Blvd, Maitland, FL 32751

/48
Est $513,679 Not Listed For Sale

1100 S Orlando Ave Unit 802, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,118 Sq Ft
- Built 1973
1100 S Orlando Ave Unit 802, Maitland, FL 32751

Last Sold Summary
- 29% Below List Price
- $644/SF
- 4 Days On Market
Last Sold Price $720,000

Last Listing Agent Julie Bombardo PREMIER SOTHEBY'S INTL. REALTY

/48
$565,000 Pending
- 3 Beds
- 2 Baths
- 1,929 Sq Ft
2136 Mohican Trail, Maitland, FL 32751

One or more photo(s) has been virtually staged. Nestled in the desirable Highland Park Estates within the highly sought-after Dommerich area and a desirable school district, this charming home offers timeless character and incredible potential to make it your own. The retro-style kitchen opens to an inviting family room highlighted by a classic brick accent wall, while the shared brick

Cheryl Geluso RE/MAX ASSURED

2136 Mohican Trail, Maitland, FL 32751
/2
$505,000 Sold Aug 26, 2025

2089 Sunderland Rd, Maitland, FL 32751
- 4 Beds
- 2 Baths
- 1,627 Sq Ft
- Built 1963
Last Sold Summary
- 4% Below List Price
- $310/SF
- 22 Days On Market
Current Estimated Value $489,343

Last Listing Agent Ahmad Hassan COMPASS FLORIDA LLC

2089 Sunderland Rd, Maitland, FL 32751

/26
Est $351,430 Not Listed For Sale

1000 S Orlando Ave Unit B33, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 952 Sq Ft
- Built 1964
1000 S Orlando Ave Unit B33, Maitland, FL 32751

Last Sold Summary
- 6% Below List Price
- $394/SF
- 42 Days On Market
Last Sold Price $375,000

Last Listing Agent Amanda Wood RE/MAX

/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
/2
$2,850,000 Sold Sep 12, 2025

640 Old Horatio Ave, Maitland, FL 32751
- 5 Beds
- 4 Baths
- 4,042 Sq Ft
- Built 2025
Last Sold Summary
- 17% Below List Price
- $705/SF
- 156 Days On Market
Current Estimated Value $2,898,000

Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

640 Old Horatio Ave, Maitland, FL 32751

/67
Not Listed For Sale

1140 S Orlando Ave Unit B15, Maitland, FL 32751
- 2 Beds
- 1 Bath
- 816 Sq Ft
- Built 1964
1140 S Orlando Ave Unit B15, Maitland, FL 32751

Last Sold Summary
- $355/SF
- 166 Days On Market
Last Sold Price $290,000

Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

/52
$675,000 Pending
- 6 Beds
- 4 Baths
- 2,484 Sq Ft
933 and 935 Robinhood Ct, Maitland, FL 32751

NEW PRICE IMPROVEMENT! Whole Duplex. 6/4 (3 bed 2 bath in each unit). The Duplex is located in a cul-de-sac on a large lot that backs up to walking trail. Oakmont neighborhood has access directly to Sunrail Maitland Station. No HOA. Unit 933 has a fireplace for those cold Florida winters. The backyard is fully fenced and has an above-the-ground pool and a fully functionable bar with electric and

Olaf Stenger KGV REALTY GROUP

933 and 935 Robinhood Ct, Maitland, FL 32751
/2
$250,000 Sold Aug 22, 2025

20 People St, Maitland, FL 32751
- Land
- 0.58 Acre
- $431,034 per Acre
Last Sold Summary
- 10 Days On Market
Current Estimated Value $249,369

Last Listing Agent Julia Meffen FLORIDA HOMES & LOANS INC.

20 People St, Maitland, FL 32751

/13
Est $414,910 Not Listed For Sale

1100 S Orlando Ave Unit 504, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,285 Sq Ft
- Built 1973
1100 S Orlando Ave Unit 504, Maitland, FL 32751

Last Sold Summary
- 6% Above List Price
- $304/SF
- 88 Days On Market
Last Sold Price $390,000

Last Listing Agent Joann Beck BECK REALTY LLC

/15
$2,150,000 Pending
- 5 Beds
- 4.5 Baths
- 4,004 Sq Ft
101 Whitecaps Cir, Maitland, FL 32751

Under contract-accepting backup offers. Under Construction. An elite expression of sophisticated design and elevated living, this remarkable residence offers a resort-style experience that stands apart in Maitland. This home is positioned on a sprawling corner lot and immediately captivates with a grand façade and undeniable curb appeal. From the moment you step inside, the experience is dramatic

Christopher Christensen ONE LUXURY INTERNATIONAL LLC

101 Whitecaps Cir, 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
Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

1140 S Orlando Ave Unit K15, Maitland, FL 32751

/2
Not Listed For Sale

1140 S Orlando Ave Unit K17, Maitland, FL 32751
- 2 Beds
- 1 Bath
- 816 Sq Ft
- Built 1966
1140 S Orlando Ave Unit K17, Maitland, FL 32751

Last Sold Summary
- $341/SF
- 13 Days On Market
Last Sold Price $278,000

Last Listing Agent Stacie Brown Kelly KELLER WILLIAMS ADVANTAGE REALTY

/20
$640,000
- 4 Beds
- 2 Baths
- 2,360 Sq Ft
2642 Brookside Ct, Maitland, FL 32751

Indulge in the epitome of modern living with this fully renovated masterpiece! Boasting a thoughtfully designed split floor plan, 4 bedrooms, and2 bathrooms, this home offers the perfect blend of space, style, and versatility. The heart of the home, the sleek kitchen, is a culinary haven equipped with stainless steel appliances, and ample counter space with upscale quartz countertops and storage.

Giancarlo Chavez KELLER WILLIAMS CLASSIC

2642 Brookside Ct, 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 $383,938

Last Listing Agent Sonia Dublis COLDWELL BANKER REALTY

518 Oak Ln, Maitland, FL 32751

/2
Not Listed For Sale

1000 S Orlando Ave Unit A6, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 952 Sq Ft
- Built 1964
1000 S Orlando Ave Unit A6, Maitland, FL 32751

Last Sold Summary
- $401/SF
- 194 Days On Market
Last Sold Price $382,000

Last Listing Agent Cristina Kaufman ALL REAL ESTATE & INVESTMENTS

/70
$525,000 Pending
- 3 Beds
- 2 Baths
- 1,577 Sq Ft
830 Faith St, Maitland, FL 32751

Under contract-accepting backup offers. Beautifully renovated 3-bedroom, 2-bathroom home featuring modern finishes and a bright, open layout. Wood-look tile flows throughout the entire home, creating a cohesive and low-maintenance living space. The stunning white kitchen is the heart of the home, complete with quartz countertops, new appliances, recessed lighting, a large island, and stylish

Randy Fontanez, II CHARLES RUTENBERG REALTY ORLANDO

830 Faith St, 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 $676,368

Last Listing Agent Kayla Watson COMPASS FLORIDA LLC

1921 Geronimo Trail, Maitland, FL 32751

/34
Est $430,983 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
- 5% Above List Price
- $319/SF
- 11 Days On Market
Last Sold Price $410,000

Last Listing Agent Laura Heidrich COLDWELL BANKER REALTY

/53
$515,000 Pending
- 2 Beds
- 2 Baths
- 1,203 Sq Ft
206 Quayside Cir Unit 302, Maitland, FL 32751

Under contract-accepting backup offers. LAKEFRONT PARADISE ON LAKE MAITLAND AND THE WINTER PARK CHAIN OF LAKES. Cue the Jimmy Buffett music as you arrive home to your own serene tropical lakefront paradise here at The Moorings on Lake Maitland. The pace feels a bit more relaxed here on the water! This beautiful, move-in ready FULL lakefront condo is located on the third floor of building 3 which

Loretta Maimone ERA GRIZZARD REAL ESTATE

206 Quayside Cir Unit 302, 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 $334,212

Last Listing Agent Shirley Welch BHHS FLORIDA REALTY

2352 Sierra Ln, Maitland, FL 32751

/2
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
- $320/SF
- 28 Days On Market
Last Sold Price $305,000

Last Listing Agent Joann Beck BECK REALTY LLC

/36
$1,075,000
- 4 Beds
- 3.5 Baths
- 2,598 Sq Ft
1610 Lyndale Blvd, Maitland, FL 32751

LOCATION, LOCATION, LOCATION! Ideally situated just off Park Avenue in the highly desirable Maitland/Winter Park area, this beautifully maintained home offers the perfect blend of charm, functionality, and convenience.Featuring 4 bedrooms and 3.5 bathrooms, the home welcomes you with elegant formal living and dining spaces enhanced by detailed trim work, crown molding, and updated lighting.

Christian Del Pino CAPITAL EQUITY REAL ESTATE CO

1610 Lyndale Blvd, Maitland, FL 32751
/30
$468,000 Sold May 10, 2025

651 Robinhood Dr, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,231 Sq Ft
- Built 1991
Last Sold Summary
- 2% Below List Price
- $380/SF
- 21 Days On Market
Current Estimated Value $463,214

Last Listing Agent Heather Unger, PA ACME REAL ESTATE FLORIDA LLC

651 Robinhood Dr, Maitland, FL 32751

/2
Est $463,520 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
- 7% Above List Price
- $361/SF
- 64 Days On Market
Last Sold Price $434,000

Last Listing Agent Francis Gilman KELLER WILLIAMS WINTER PARK

/5
$4,999,000 New Construction
- 5 Beds
- 8 Baths
- 6,466 Sq Ft
360 Lake Seminary Cir, Maitland, FL 32751

Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space,

Mel Bernstein PREMIER SOTHEBYS INT'L REALTY

360 Lake Seminary Cir, 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 $406,650

Last Listing Agent Gale Milgrim KELLER WILLIAMS WINTER PARK

2132 Tortoise Shell Dr, Maitland, FL 32751

/39
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
- $401/SF
- 0 Days On Market
Last Sold Price $500,000

Last Listing Agent Lisa Shear FANNIE HILLMAN & ASSOCIATES

/13
$419,900
- 4 Beds
- 2 Baths
- 1,680 Sq Ft
385 Lime St, Maitland, FL 32751

Wonderful investment opportunity in historic Eatonville. Large corner lot. Roof was replaced in 2023. HVAVs and water heaters were replaced in 2021. Updated kitchen and bathroom were updated in both bathrooms. The property is completely fenced. There are (2) parking spaces for each unit. Side (1) is currently leased at $1,315 each month. Side #2 is vacant. Side #2 was just updated.is also $1,315

Marian Coaxum KELLER WILLIAMS REALTY AT THE PARKS

385 Lime St, Maitland, FL 32751
/2
$1,700,000 Sold Apr 24, 2025

125 Stone Hill Dr, Maitland, FL 32751
- 9 Beds
- 7 Baths
- 8,190 Sq Ft
- Built 2004
Last Sold Summary
- 15% Below List Price
- $208/SF
- 24 Days On Market
Current Estimated Value $1,913,296

Last Listing Agent Natalie Citarelli CITARELLI REALTY GROUP LLC

125 Stone Hill Dr, Maitland, FL 32751

/50
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
- $367/SF
- 64 Days On Market
Last Sold Price $349,000

Last Listing Agent David Perez COLDWELL BANKER REALTY

/74
$234,000
- 4 Beds
- 2 Baths
- 1,372 Sq Ft
1175 Lake Shadow Cir Unit 4308, Maitland, FL 32751

Experience true resort-style living at its finest in this lovely 4-bedroom, 2-bath condominium in the beautiful, gated community Visconti West. As you enter the home, you are welcomed by an open and spacious floor plan filled with abundant natural light, vaulted ceilings and decorative cutouts. Enjoy a split-plan layout that offers comfort and privacy for family and guests. The kitchen features a

Julie Ruh COLDWELL BANKER REALTY

1175 Lake Shadow Cir Unit 4308, Maitland, FL 32751

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