One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly

Brian Scanlon SCANLON REALTY GROUP LLC

*Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental

Ryan Leitter CHARLES RUTENBERG REALTY ORLANDO

RECLAIM YOUR TIME: Stop sacrificing your sleep and evenings to the I-4 commute. Located in the gated community of Montacino, this 3-bedroom, 2.5-bath (one owner) townhome sits at a convenient midpoint between Downtown Orlando and Sanford—approximately 15 minutes to each—offering everyday convenience for work and play. Snowbirds will appreciate the lock-and-leave ease and proximity to Orlando’s

Shirley Jones COLDWELL BANKER RESIDENTIAL RE

Million Dollar Lakefront View of Lake Killarney from Private Balcony and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when you walk through the Door! Kitchen has been improved with raised Ceilings and expansive Wood

Janice Erickson REALCOM REAL ESTATE SERVICES INC

Welcome to 958 Dupont Ave, a home that exudes charm and functionality. The kitchen is a chef's dream, boasting all stainless steel appliances that add a sleek, modern touch. Step outside to a spacious, fenced-in backyard, perfect for privacy and outdoor activities. Enjoy leisurely afternoons or entertain on the covered patio, a delightful extension of the living space. A storage shed provides

Karen Albright OPENDOOR BROKERAGE LLC

Discover sophisticated modern living at 607 Ellen Drive, a stunning new construction home by the acclaimed Lazarus Homes in the heart of Winter Park. This impeccably designed 2,812-square-foot residence showcases contemporary architecture with clean lines, high ceilings, and an abundance of natural light throughout. The open floor plan seamlessly connects living spaces, creating an ideal setting

Kelly Price KELLY PRICE & COMPANY LLC

Luxury lakefront living at its finest awaits at "The Moorings" on Lake Maitland Chain of Lakes.Perfectly positioned on the first floor, this stunning two-bedroom, two-bath residence offers breathtaking lake views from nearly every room, creating a serene and sophisticated backdrop for everyday living. Completely renovated with impeccable attention to detail, the home features designer epoxy

Donnamarie Ebanks COLDWELL BANKER REALTY

PRICE REDUCED!!! Rare opportunity for a "Jewel of Park Lake" spacious 3 bedroom, 2 bath villa with beautiful wooded view in the desirable Park Lake community of Maitland. MOVE-IN READY!!! Assigned/dedicated Parking. Close to major transportation routes, employment centers, Park Avenue/Winter Park, Altamonte Springs and downtown Orlando. HVAC replaced in 2021. NEW Appliances flooring and paint in

Michael Dabby DABBY REAL ESTATE ADVISORS, LLC

Welcome to this distinctive 3-bedroom, 3-bath, two-story residence in Winter Park, offering a rare and versatile layout ideal for multi-generational living, college roommates or those seeking flexible space. Thoughtfully designed with two separate living areas, this home provides privacy, functionality, and room to grow—all just minutes from major highways and the charm of downtown Winter Park.

Jill Healey KELLER WILLIAMS WINTER PARK

ANOTHER PRICE REDUCTION!Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas!Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters, Stainless Steel Appliances, Raised Ceiling with

Janice Erickson REALCOM REAL ESTATE SERVICES INC

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

Under Construction. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 1⁄2 baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that easily flexes as a

Marie Ledbetter COLDWELL BANKER RESIDENTIAL RE

Welcome to Retreat at Lake Bosse — a rare opportunity in this highly sought-after, single-street community featuring a private dock exclusively for homeowners and their guests. This beautifully designed 4-bedroom, 2-bath home offers nearly 2,100 sq. ft. of thoughtfully planned living space. Step inside to an open, airy floor plan centered around a dream kitchen with 42" upper cabinets, crown

Lora King HOMEVEST REALTY

Welcome home to this beautifully 3 bedroom, 3 full bath 1,435 sq ft townhome located in the quiet and well maintained Rosemont Green community, featuring a community pool and ample parking. Thoughtfully designed across two levels, this residence offers a flexible floor plan ideal for both comfortable living and entertaining. As you enter, the kitchen sits to the left and features a charming nook

Monica Vega Stiskin PREFERRED REAL ESTATE BROKERS

This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water is included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to

Debbie Fussell KELLER WILLIAMS REALTY AT THE PARKS

Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor condo in the heart of charming Winter Park, FL 32789! Meticulously updated since 2023, this home blends modern luxury with effortless comfort and is truly move-in ready.As you step inside, you’ll be greeted by elegant porcelain tile flooring throughout—offering both durability and a look that’s easy to

Eric Campbell LPT REALTY, LLC

FIRST TIME ON THE MARKET! ULTRA-RARE GROUND FLOOR CONDO IN DOWNTOWN WINTER PARK'S LACHEN HOUSE – AVAILABLE FOR RENT OR PURCHASE! This is your chance to secure a highly coveted ground floor unit in one of Winter Park's most desirable locations. Available for rent at $3,800/month or purchase at $635,000 with quick move-in or quick closing possible!This stunning 2-bedroom, 2-bath condo has been

Kelly Price KELLY PRICE & COMPANY LLC

Welcome to a home that invites you in — and then continues to surprise you at every turn. Step inside the main residence and you’re greeted by 1,957 square feet of warm, comfortable living space, where an open yet defined layout creates the perfect balance of function and flow. The separate living and dining areas offer room to gather, entertain, and unwind, while large windows fill the home with

Janay Thomas EXP REALTY LLC

Under Construction. Renderings available soon. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 1⁄2 baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright

Marie Ledbetter COLDWELL BANKER RESIDENTIAL RE

Stunning 4-Bed, 3-Bath Fully Renovated Home – Modern Luxury Meets Timeless DesignThis exceptional home has been completely gutted and rebuilt from the ground up with permits by licensed contractors, offering 4 spacious bedrooms and 3 luxurious bathrooms. One bedroom is perfect as a private office, featuring elegant barn doors, while the master suite is a true retreat with double sinks, bench

Fariba Azari Rad INVESTOR'S REAL ESTATE LLC

Attention lake enthusiasts! This is your opportunity to enjoy true waterfront living without the cost or maintenance typically associated with it. Located on beautiful Lake Killarney in sought-after Winter Park you will enjoy an array of amenities including a private boat ramp, a large open boat dock where you can feed the fish and turtles, picnic areas, clubhouse and resort style community pool

Lora King HOMEVEST REALTY

Welcome home to 1405 Black Willow Trail! This beautifully updated 3-bedroom, 2-bath residence features a desirable split floor plan and vaulted ceilings that create a bright, open, and airy feel throughout the main living spaces. The home is truly move-in ready with luxury vinyl plank and tile flooring throughout—no carpet—and a freshly painted neutral interior that complements any décor. The

Virginia Bellhorn WATSON REALTY CORP