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ELLNO WILLO - O6398694 - 1565 FOREST AVE, WINTER PARK, FL 32789 Just Added on 04/14/2026 11:56AM
$1,750,000 | Single Family Home | 4 beds | 2.0 baths
One or more photo(s) has been virtually staged. Set apart from the ordinary, this historic Winter Park residence offers a rare opportunity to own a home rich in character and authenticity. Homes like this, with timeless architectural detail and enduring charm, rarely come to market, especially in such a premier location just steps from the shores of Lake Virginia. Surrounded by multi million dollar estates, this 4 bedroom, 2 bath home blends classic warmth with everyday livability. Original wood floors, a wood burning fireplace, and thoughtfully designed living spaces reflect a level of craftsmanship and character that simply cannot be replicated. The spacious dining room is perfect for hosting memorable family gatherings, while the updated kitchen with wood cabinetry offers both function and charm. Upstairs, a versatile loft space provides flexibility for a media room, office, or play area, complete with peekaboo views of Lake Virginia that create a subtle connection to the surrounding landscape. Adding to the home’s appeal is a detached 20 x 20 studio flooded with natural light and offering endless possibilities, ideal for an artist’s retreat, home office, gym, or guest space.This is more than a home, it is an opportunity to own a piece of Winter Park’s character and history. Set among some of Winter Park’s most prestigious homes, this property delivers an unbeatable lifestyle, walkable to all that Park Avenue has to offer, surrounded by luxury, and full of potential to enjoy, enhance, or reimagine.
Listing is courtesy of: NORDQUIST & COMPANY INC
EASTGATE SUB - O6398118 - 102 BELL PL, WINTER PARK, FL 32792 Just Added on 04/14/2026 8:01AM
$1,399,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Step into elevated Florida living with this stunning brand-new residence, where modern design meets lasting quality. Constructed with solid block and steel framing for superior durability, this home is quietly nestled on a cul-de-sac in one of Winter Park’s most up-and-coming areas—without the restrictions of an HOA. Just moments from Interlachen Country Club and the charming Lakemont Heights neighborhood, the location offers both prestige and convenience. From the moment you enter through the impressive double doors, you’re welcomed by a light-filled, open-concept design. Soaring 10-foot ceilings and elegant 8-foot doors create an airy, expansive feel, while abundant natural light highlights the home’s sleek, contemporary finishes. At the heart of the home, the chef-inspired kitchen truly shines. Outfitted with luxurious quartz countertops, stainless steel appliances, and a custom LED-lit wine display, it’s designed to impress. The seamless flow into the living and dining spaces—along with views of the backyard—makes it perfect for entertaining or everyday connection. The primary suite is a private sanctuary, offering a spa-like escape with dual vanities, a spacious dual-entry shower, and a freestanding soaking tub designed for relaxation. With three additional bedrooms, a dedicated office, and 3.5 beautifully appointed bathrooms, this thoughtfully designed single-story home provides nearly 2,500 square feet of flexible living space. Outdoors, your personal retreat awaits. Enjoy year-round Florida living on the covered lanai, complete with a built-in summer kitchen and a custom-designed pool—ideal for hosting or unwinding. The fully fenced yard features new vinyl fencing, fresh sod, and an automated sprinkler system for effortless maintenance. Perfectly positioned near Phelps Park, the Winter Park YMCA, Lakemont Elementary, and an array of top-tier shopping and dining destinations, this home delivers the ideal blend of privacy, craftsmanship, and everyday luxury.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK
LAWNDALE - O6398673 - 1618 INDIANA AVE, WINTER PARK, FL 32789 1 Day on yellowkey
$685,000 | Apartment | 4 beds | 2 car
Beautiful income-producing duplex located in the highly desirable Winter Park area! This well-maintained property features two units, each offering 2 bedrooms, 1 bathroom, and a dedicated utility room for added convenience. Both sides provide functional layouts with comfortable living spaces, making it ideal for tenants or owner-occupants looking to offset their mortgage. Situated on Indiana Ave, this property is just minutes from Park Avenue, shopping, dining, and major roadways, offering both convenience and strong rental appeal. Whether you're looking to expand your investment portfolio or live in one unit while renting the other, this duplex presents a fantastic opportunity in a prime location.
Listing is courtesy of: NATIONAL REAL ESTATE
EASTBROOK SUB UNIT 05 - O6398603 - 1589 VIBURNUM LN, WINTER PARK, FL 32792 1 Day on yellowkey
$365,000 | Single Family Home | 3 beds | 2.0 baths | 2 car
Newly renovated 3 bedrooms 2 bath with flex room for home office or entertainment. Large lot with huge carport and storage room. Solar roof with attractive low payments to offset public utility bill. New LVP flooring throughout with tiles for bathrooms. New cabinets, appliances and relatively newer roof and AC for move-in ready home.
Listing is courtesy of: LOKATION
GOLFSIDE SEC 3 - O6398533 - 1210 FAIRWAY DR, WINTER PARK, FL 32792 1 Day on yellowkey
$549,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Welcome home to this beautiful single-story Pool home in the Golfside community of Winter Park. Offering 3 bedrooms, 2 bathrooms, and 1,737 square feet of living space, this home features a spacious and inviting layout designed for both everyday living and entertaining. Upon entry, you are welcomed into the living room, while an adjacent dining room combination provides additional flexible gathering space. The family room offers French door access to the covered rear patio, creating a seamless indoor-outdoor flow to the expansive backyard, perfect for hosting family and friends.The kitchen opens to the main living areas and is equipped with stainless appliances, stone countertops, and ample cabinet space. A hallway just off the family room leads to all three bedrooms and two full bathrooms, including a spacious primary suite with an ensuite bath. Additional features include engineered wood throughout the main living areas, extra storage closets, an interior laundry room, and a 2-car garage.Ideally located near Winter Pines Golf Club, this home also offers convenient access to I-4 and SR-417, making it easy to reach shopping, dining, entertainment, downtown Orlando, the airport, area attractions, and the beaches.
Listing is courtesy of: CENTRAL FLORIDA PRIME REAL ESTATE LLC
LAWNDALE - O6398421 - 1540 MILLER AVE, WINTER PARK, FL 32789 1 Day on yellowkey
$1,399,900 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by SGC Construction! This stunning new Mid-Century Modern–inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and comfort. Step onto the inviting front porch and through the elegant entryway to discover a spacious, open floor plan filled with natural light. Just off the foyer, you’ll find a flexible fourth bedroom or private study with a full bath—ideal for a home office or serene guest suite. The heart of the home is the gourmet kitchen, featuring quartz countertops, custom cabinetry, and a premium Bosch appliance package including a 36" gas cooktop. The kitchen flows seamlessly into the living and dining areas—perfect for entertaining or family gatherings. Enjoy Florida living at its finest on the covered lanai, overlooking your sparkling pool and lushly landscaped backyard—your own private retreat. The first-floor primary suite offers a spa-inspired bath with dual vanities, a freestanding soaking tub, and a spacious walk-in closet with custom shelving. A convenient laundry area is thoughtfully located just off the suite. Upstairs, a large bonus room with a closet offers versatility as a fifth bedroom, game room, or home office. Two additional bedrooms feature walk-in closets and share a beautifully appointed bath with dual sinks. An upstairs laundry room with a sink and plenty of natural light adds everyday convenience. The photos shown are of the same model in another location. Finishes will vary. Located near top-rated schools, local parks, and all that Winter Park has to offer — this home truly has it all. Schedule your private showing today before this exceptional new build is gone!
Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION
LAUREL SPGS - O6398450 - 3054 BLUEBROOK DR, WINTER PARK, FL 32792 1 Day on yellowkey
$427,500 | Single Family Home | 3 beds | 2.0 baths | 1 gar
"Open the Doors to Your Dreams" of owning an Affordable Home with a pool in Winter Park. The home features a Spacious Kitchen with Upgraded Cabinets, and stone countertops; Primary bedroom suite is amazing. You will love the layout and upgraded primary bathroom; Beautiful Porcelain tile flooring throughout the home; Large family room with fireplace; Large screened back porch/LANAI. And there is an inground pool in the back yard. You will enjoy entertaining in this home featuring a gourmet kitchen with granite countertops, and stainless steel appliances. This property may qualify for Seller Financing (Vendee). If property was built prior to 1978, Lead Based Paint Potentially Exists. Come tour this home today. We expect this one to sell quickly.
Listing is courtesy of: WEATHERSPOON REALTY INC
COLONIES - S5147382 - 3021 AARON BURR AVE #3, WINTER PARK, FL 32792 1 Day on yellowkey
$140,000 | Condo | 2 beds | 2.5 baths
Townhouse opportunity—ideal for either personal residence or investment—featuring 2 bedrooms and 2.5 bathrooms. Conveniently located near supermarkets, shops, universities, and public transportation. At closing, all outstanding HOA special assessments will be paid off. The Townhome is rent $1,600. The unit is located in Winter Park Area HOME GUARANTY OF AMERICA HWA 13 MONTH INCLUDED.
Listing is courtesy of: NAIM REAL ESTATE LLC
ALBERT LEE RIDGE 1ST ADD - O6398273 - 950 HANOVER AVE, WINTER PARK, FL 32789 3 Days on yellowkey
$470,000 | Single Family Home | 3 beds | 2.0 baths | 1 gar
Preferred lender credit available. Welcome home to your peaceful retreat tucked away near the end of a quiet street with views of Lake Wilderness. Completely updated in 2017, move-in ready so you can lock and leave with peace of mind to enjoy the everyday lifestyle of Winter Park and Central Florida this amazing location offers. Full updates made in 2017 include new roof, plumbing, electrical, windows, recessed lighting, a/c unit, and more. Natural sunlight flows throughout the home reflecting off the refinished wood floors creating an inviting and cozy environment. The open kitchen features quartz countertops, glass crafted tile backsplash, custom cabinets, breakfast bar and stainless steel appliances. Feel refreshed and relaxed as you step into the primary suite with barn doors leading into the spa-inspired bathroom, complete with dual vanities and a large walk-in tiled shower. The backyard is fully fenced and the outdoor patio is screened-in and covered. Extra storage space can be used in the outdoor shed or the one car attached garage. No HOA and not in a flood zone. The property’s exceptional location offers close proximity to I-4 East and West, upscale award-winning Winter Park restaurants and boutiques, Winter Park Village, WP9 Golf Course, Park Ave, and the upcoming state-of-the-art Lifetime Fitness center which features over 85,000 SqFt and 5 acres of the best that wellness amenities have to offer. Nearby EV charging stations located within 2 miles away make sustainable living effortless. Rare opportunity to settle into or invest in a peaceful updated retreat located in the highly desirable and vibrant community of Winter Park.
Listing is courtesy of: COMPASS FLORIDA LLC
ALOMA TRAILS - O6398259 - 7485 ALOMA PINES CT, WINTER PARK, FL 32792 4 Days on yellowkey
$390,000 | Townhouse | 3 beds | 2.5 baths | 2 gar
Experience the perfect blend of luxury and convenience in the highly sought-after GATED community of Aloma Trails. This meticulously maintained 3-bedroom, 2.5-bathroom townhome, built in 2017, offers 1,787 sq. ft. of living space designed for comfort and modern style. Step inside to find an inviting open-concept first floor featuring beautiful ceramic tile flooring and high ceilings. The gourmet chef’s kitchen is a true standout, boasting upgraded granite countertops, a stylish tiled backsplash, 42” solid wood cabinetry, and a large island with plenty of breakfast bar seating. The full suite of stainless steel appliances makes this kitchen as functional as it is beautiful. The second level features plush carpeting throughout the bedrooms for ultimate comfort. The oversized Master Suite is a private sanctuary, complete with a massive walk-in closet and a spa-like en suite bathroom featuring a glass-enclosed shower, dual-sink vanity, and expansive cabinetry. Two additional well-appointed bedrooms share a second full bath, while the dedicated interior laundry closet adds a layer of daily convenience. Uniquely positioned with a spacious 2-car garage and a private paved driveway, this home easily accommodates multiple vehicles. The community of Aloma Trails provides a true "lock-and-leave" lifestyle with hassle-free lawn care and pristine common areas included in the HOA. Active lifestyles will thrive with the Cady Way Trail and Cross Seminole Trail just steps from your front door. For fitness buffs, Crunch Fitness is located directly across from the community entrance. Retail: 3 minutes to Walmart, Costco, and Publix. Education: Zoned for top-rated Seminole County Schools and minutes from UCF and Full Sail University. Entertainment: Short drive to the world-class dining and shopping of Park Avenue in Winter Park. Commute: Easy access to SR 417 puts you at the airport in 20 minutes or the beach in just 40! Don't miss your chance to own a piece of Winter Park luxury in a premier gated enclave.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC
LOST CREEK - O6397396 - 3110 HEARTLEAF PL, WINTER PARK, FL 32792 4 Days on yellowkey
$629,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar
Nestled in the upscale Lost Creek community, this maintained 4-bedroom, 3-bathroom screened pool home offers the perfect blend of comfort and natural beauty with over an acre of land that extends all the way to Howell Creek. Upon entering, you are greeted by high ceilings and an open-concept great room layout. The formal living room flows seamlessly into the dining room, creating an ideal setting for entertaining. Beyond, a spacious family room opens to views of the pool, while the adjacent gourmet kitchen and breakfast area complete the heart of the home. The kitchen features New quartz countertops and stainless steel appliances. The main level is home to a spacious primary bedroom, offering serene views of both the pool and surrounding forest. Sliding doors provide direct access to the pool deck, while inside you'll find a generous walk-in closet, a double-sink vanity, a relaxing garden bathtub, and a separate shower. Additional guest bedroom and a full guest bathroom complete the main floor. Upstairs, a charming loft with a built-in desk provides the perfect work-from-home or study retreat, accompanied by two additional bedrooms and a shared bathroom. Outside, the screened pool backing up to a natural wooded area with no rear neighbors is your private oasis — perfect for year-round Florida living. Winter Park is close to numerous shops and eateries along with easy access to major expressways. You get all this in a great school district. Sod intalled(2026), Quartz Countertops(2026), Pool pump(2026), Range & Dishwasher(2026), Roof(2022)
Listing is courtesy of: FUSILIER MANAGEMENT GROUP
PARKLANDO - O6397997 - 2702 PARKLAND DR, WINTER PARK, FL 32789 4 Days on yellowkey
$1,175,000 | Single Family Home | 5 beds | 3.0 baths | 2 gar
Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace that anchors the main living space. The renovated kitchen is thoughtfully designed with both everyday living and entertaining in mind, flowing seamlessly into the dining and living areas. A dedicated office provides the perfect work from home setup or quiet retreat, while the flexible layout offers plenty of room for guests, growing families, or multi generational living. Outside, enjoy a private backyard with a charming fire pit and rock gathering are deal for relaxing evenings or hosting friends. The oversized lot also offers ample space to add a pool and create your own backyard oasis. Additional highlights include a 2-car garage, roof replaced in 2018, home repiped in 2019, and updated AC for peace of mind. This is a rare opportunity to own a move-in ready home in one of Winter Park’s most sought after neighborhoods, walking distance to the Audubon Park Garden District with amazing dining, and shopping.
WINTER PARK VILLAGE - O6397694 - 2408 LAFAYETTE AVE, WINTER PARK, FL 32789 4 Days on yellowkey
$1,495,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar
This custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set apart for quiet pursuits. The chef’s kitchen opens naturally to the great room and boasts a large island, top-of-the-line Thermador appliances, complemented by the sleek quartz countertops that offer both style and functionality. Conveniently equipped with two sets of washers and dryers, this home ensures efficiency and ease for the busiest of households. Retreat to the master suite, where luxury meets serenity. A massive walk-in closet provides ample storage, while the spa-like master bath invites relaxation with its elegant design and premium features. The indoor outdoor flow is easy with the huge set of glass sliders leading to the covered porch equipped with drop down screens. Enjoy the summer kitchen and sparkling pool while entertaining family and friends. This home is a true gem that combines thoughtful details with sophisticated style.
Listing is courtesy of: CORCORAN PREMIER REALTY
LAKE VIRGINIA PT REP - O6397480 - 543 E LAKE SUE AVE, WINTER PARK, FL 32789 5 Days on yellowkey
$1,875,000 | Single Family Home | 4 beds | 4.5 baths | 3 gar
Under contract-accepting backup offers. Welcome to Timberlane Shores—one of Winter Park’s most desirable neighborhoods! This beautiful 4-bedroom, 4.5-bath home sits on over a third of an acre in a quiet, tucked-away location with gorgeous updated landscaping. Inside, you’ll find wide-plank hardwood floors throughout and a thoughtfully designed floor plan with separate living and dining rooms plus a spacious family room. The bright kitchen features white cabinetry with pull-out drawers, marble countertops, subway tile backsplash, and newer appliances (2018), including a Sub-Zero refrigerator and Wolf gas 4 burner range. The kitchen opens to a bright sunroom with beautiful wood-like tile floors laid in a herringbone pattern (2018). Such a great space that is filled with natural light—perfect as a casual gathering space or playroom, making this an ideal home for entertaining. The sunroom overlooks the enormous backyard space and large pool area with custom designed pavers (2023). A downstairs guest suite with full bath provides comfort and privacy, while a dedicated office with built-in desks and brand new carpet adds functionality. Upstairs, the oversized primary suite boasts a beautifully appointed bathroom with dual sinks, marble countertops, soaking tub, and separate walk-in shower, along with a custom walk-in closet. Two additional upstairs bedrooms each offer en-suite baths, including one renovated in 2021. Recent updates include new windows (2017), solid wood front door (2021), renovated bath (2021), two new AC units and duct cleaning (2024), and a new roof (2024). This exceptional home offers the perfect blend of style, comfort, and location—truly a must-see.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES
VILLAGE GREEN - O6396985 - 7529 VILLAGE GREEN DR, WINTER PARK, FL 32792 5 Days on yellowkey
$325,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
***Multiple Offers Received. Please submit your highest and best offer by Monday, April 13th at 12 noon.***Buyer incentives you don't want to miss! This home qualifies for a 1% lender credit with our preferred lender. Location meets affordability with this rare opportunity in Winter Park with no HOA! With some TLC, this 3 bedroom, 2 bath home offers endless potential to make it your own. Major updates provide peace of mind, including a metal roof (2014), water heater (2024), and updated electrical panel (2012). Situated on a spacious .28 acre lot, the property features a fully fenced backyard- perfect for pets, play, or future outdoor living enhancements. Inside, you'll find a functional layout with a split-bedroom floor plan, a generous living room, and a separate family room for added flexibility. The kitchen offers ample cabinet space and room for casual dining. A 2 car garage and extended driveway provide plenty of parking. Ideally located near top rated Seminole County schools, with convenient access to UCF, SR 417, shopping, dining, and area attractions. Dont miss this incredible opportunity to own in a prime location with room to grow! Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY
LAKESIDE ESTATES - O6397250 - 1453 VIA SANGRO PL, WINTER PARK, FL 32792 5 Days on yellowkey
$995,000 | Single Family Home | 4 beds | 3.0 baths | 3 gar
Welcome to refined Florida living in the highly sought-after gated community of Lakeside Estates, one of Winter Park’s most exclusive neighborhoods, where homes rarely come to market. With only 39 residences, this intimate lakefront community offers a level of privacy, prestige, and curb appeal that is increasingly difficult to find. From the moment you pass through the impressive gated entrance framed by a beautifully designed pond, elegant stone wall, and striking fountain, you immediately sense that Lakeside Estates is something special. This Mediterranean-inspired residence showcases timeless architectural design with a stunning stone-accented tower entry, graceful arched architecture, and a classic barrel tile roof, all complemented by a beautifully maintained paver driveway and a welcoming 8-foot front door. Inside, thoughtful craftsmanship is evident throughout, with colonial-style crown molding, designer finishes, and wood-look porcelain plank tile flooring that delivers the warmth of hardwood with exceptional durability. At the heart of the home, the chef’s kitchen is designed for both everyday living and entertaining, featuring white shaker cabinetry with crown molding, quartz countertops with elegant marble-inspired veining, stainless steel appliances, and a double oven. A beautifully appointed butler’s pantry with a built-in wine rack enhances both convenience and sophistication. The versatile floor plan includes a dedicated office, four bedrooms, spacious living areas, and generously sized rooms, creating flexibility for modern lifestyles. The primary suite provides a private retreat with spa-inspired features and ample storage. Step outside to your own backyard oasis featuring an enclosed saltwater pool, peaceful water views, and pre-plumbing for a future outdoor kitchen, making this outdoor space ideal for year-round entertaining. A convenient full pool bath provides easy access for guests while enjoying the outdoor living areas. Additional highlights include wall-mounted garage storage, kayak storage, and thoughtful design details throughout. Residents of Lakeside Estates enjoy access to a community dock where fishing and kayaking are possible, along with a playground and beautifully maintained common areas, all supported by an HOA that maintains the entrance and shared spaces. Ideally located in Winter Park and zoned for highly regarded schools, this home offers a rare opportunity to own within a private gated community where availability is limited, and demand remains strong.
WINTER PARK OAKS - O6397460 - 119 OAK GROVE RD, WINTER PARK, FL 32789 5 Days on yellowkey
$285,000 | Single Family Home | 3 beds | 2.0 baths | 1 gar
Charming 3-bedroom, 2-bath home in the heart of desirable Winter Park. Bright and inviting layout with comfortable living spaces and plenty of natural light. Enjoy a private backyard perfect for relaxing or enteraining. Conveniently located near shopping and dinning.
Listing is courtesy of: INT'L PROFESSIONAL REALTY INC
STOVINS SUB - O6396594 - 135 W SWOOPE AVE, WINTER PARK, FL 32789 6 Days on yellowkey
$2,540,000 | Townhouse | 3 beds | 3.0 baths | 2 gar
Luxury living in Winter Park 32789 in this well-appointed, fee-simple townhouse just steps from Park Avenue, with no HOA or condo fees. Three-story home features refinished hardwood floors (Knight Flooring), high ceilings, crown moldings and a PRIVATE ELEVATOR for easy access to all levels. The first floor offers a flexible bedroom, currently used as an office and bedroom along with a full bath, spacious laundry room with quartz counters, and plenty of storage. On the second floor, you’ll find an open living and dining area with a gas fireplace, built-ins, plus a large screened porch with a retractable screen and summer kitchen, ideal for entertaining. The kitchen includes stainless appliances, gas cooktop, quartz island, built-in breakfast banquette seating and bar. Upstairs, the third floor has a second bedroom with en-suite bath and a generous primary suite with custom large walk-in closet and a bright Florida room with French doors and lots of windows. The primary bath features dual granite quartz, lighted mirrors, spa tub and separate shower. Additional highlights include a new roof, A/C systems updated in 2018 and 2024, landscaping improvements, a two-car garage with extra parking spaces, smart home features and a garage refrigerator that conveys. All of this in a highly walkable location near shops, dining, parks, and golf, without the upkeep of a yard. Ava, Boca, Prato, Imperial, Garp & Fuss restaurants are steps away! Saint Margaret Mary is across the street. Enjoy the immaculate public Winter Park Nine Golf Course and historic Casa Feliz for events and concerts and Morse Museum housing the comprehensive works by Louis Comfort Tiffany. Multiple events in the park - Winter Park Arts Festival, holiday events and tree lighting, popcorn in the park movies, live music and more! Furnishings may be available.
WATERFALL COVE/WINTER PARK - O6396190 - 1695 LEE RD #D211, WINTER PARK, FL 32789 6 Days on yellowkey
$115,000 | Condo | 2 beds | 1.0 baths
Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom. Durable vinyl flooring with cozy carpeted bedrooms with a spacious walk in in closet in the primary bedroom. You will get a private balcony — perfect for morning coffee or evening relaxation and the convenience of your our laundry with washer and dryer hookups included. This condo is perfectly located in a desirable area of Winter Park close to tons of and amenities. Currently being rented for $1550/month
WINTER PARK PINES PATIO HOMES - O6397291 - 736 WARRENTON RD, WINTER PARK, FL 32792 6 Days on yellowkey
$300,000 | Half Duplex | 2 beds | 2.0 baths | 1 gar
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Renovated 2 bedroom, 2 bathroom villa in a prime Winter Park location, ready for its next owner. Walk into a spacious, light and bright foyer with fresh interior paint and sliding doors that lead out to the patio, bringing in tons of natural light. The seller has removed all popcorn ceilings (a huge upgrade), and the property features laminate flooring throughout most of the main living areas. The main living space has vaulted ceilings and an open layout with room for both living and dining, and sliding glass doors leading out to the patio. The kitchen has been updated with new stainless steel appliances and new countertops, and offers a closet pantry along with a bay window that brightens the space. The primary suite is set toward the back of the home with high ceilings, its own sliding doors to the patio, a walk-in closet, and a renovated bathroom with a large walk-in shower. The split floor plan places the second bedroom near the front by the foyer, with a renovated full bathroom just next to it—great for guests or a home office. The backyard offers a blank canvas to create your own oasis, with a covered patio, a large screened porch, and a fully fenced private yard—hard to find with a villa! Additional highlights include a one-car garage with washer/dryer hookup, new light fixtures, and fresh interior paint. Located in the Winter Park Pines just minutes from iconic Park Avenue shopping and dining and downtown Winter Park. Across from Full Sail and a short drive to UCF. Call today to schedule your private showing!
GREEN OAKS REP 02 - O6396611 - 800 JUANITA RAEL, WINTER PARK, FL 32789 6 Days on yellowkey
$2,300,000 | Single Family Home | 5 beds | 4.0 baths | 2 gar
Welcome to an exceptional opportunity in the highly desirable Park Grove community, an impeccably updated one-story residence ideally situated just moments from the vibrant shops and dining of Park Avenue and all that downtown Winter Park has to offer. With charming curb appeal, pristine landscaping and timeless architectural appeal, this home makes a stunning first impression. Inside, a thoughtfully designed floor plan offers seamless flow, perfectly suited for both everyday living and effortless entertaining. Beautiful wood flooring spans the main living areas, while the Florida room showcases distinctive Mexican tile, adding warmth and character. Designer lighting, curated tile selections and stylish wallpaper accents create a bright, inviting aesthetic throughout. The formal sitting room, complete with custom built-ins and an elegant dining room provide refined gathering spaces. At the heart of the home, a light-filled kitchen opens to the spacious family room, where a cozy wood-burning fireplace serves as a focal point. The adjacent Florida room is lined with windows, offering serene views of the sparkling pool and lush, private backyard. The generously sized primary suite is thoughtfully positioned for privacy, featuring its own wood-burning fireplace, a large walk-in closet and a beautifully appointed ensuite bath with dual vanities and an oversized walk-in shower. Four additional bedrooms are located on the opposite side of the home, two of which include ensuite baths, ideal for guests or multi-generational living. Outdoor living is equally impressive, with a beautifully paved lanai overlooking the pool and ample space for alfresco dining, entertaining and relaxing poolside. Tucked away in one of Winter Park’s sought-after neighborhoods, this home offers tranquility and convenience, with easy access to downtown Orlando, major hospitals, top-rated public and private schools and key roadways. A rare blend of style, comfort and location; this is Florida living at its finest.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY
LANDINGS AT HAWKS CREST - O6396971 - 1369 BLUE STEM LN, WINTER PARK, FL 32792 7 Days on yellowkey
$825,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Nestled in one of the most sought-after neighborhoods in Winter Park, this exceptional gated residence offers the perfect blend of elegance, comfort, and modern efficiency. Ideally located just five minutes from top-rated private schools, this two-story single-family home is designed for both luxurious living and everyday functionality. Upon entry, you are welcomed by a dramatic grand foyer featuring soaring ceilings of nearly 20 feet, creating an impressive and light-filled living space. The open layout seamlessly connects the main living areas, ideal for entertaining and family gatherings. This thoughtfully designed home features 4 spacious bedrooms and 3.5 bathrooms, including dual primary suites—one conveniently located on the main level and another upstairs—providing flexibility for multi-generational living or guest accommodations. A dedicated private office on the first floor offers the perfect work-from-home environment. Step outside to a beautifully maintained backyard with premium artificial turf, fully fenced for privacy, and a screened rear patio—perfect for relaxing or enjoying Florida’s outdoor lifestyle year-round. Extensively upgraded throughout, the home showcases high-quality finishes with no carpet—featuring elegant flooring and tile across all living areas, along with a solid wood staircase that adds warmth and sophistication. The garage is equally well-appointed with a premium epoxy-coated floor, offering both durability and a clean, polished look. Energy efficiency is a standout feature of this home, equipped with a tankless water heater for on-demand hot water and reduced energy consumption, as well as solar panels that help significantly lower utility costs. This is a rare opportunity to own a meticulously upgraded home in a prime Winter Park location—ideal as a primary residence or a high-potential investment property.
Listing is courtesy of: U S GLORY REALTY
SUBURBAN HOMES - O6396378 - 4923 N MAGNOLIA AVE, WINTER PARK, FL 32792 7 Days on yellowkey
$390,000 | Single Family Home | 3 beds | 2.0 baths | 1 car
Charming MOVE-IN Ready Solid Block 3 bedroom, 2 bath Winter Park home. This home features updated kitchen and baths, newer flooring, newer Roof- 2021, Water heater-2023, AC-2016. The home has been re-plumbed and offers newer windows-2018. Beautiful Tongue-N-Grove Woodwork covers the ceiling & walls Bonus room/Den. The home offers a split floor plan and is constructed with plaster walls, its solid and energy efficient. The home is zoned for Top-Rated, sought after Winter Park High School, Maitland Middle and Lakemont Elementary. The very best location. This one won't last long..............
Listing is courtesy of: A+ REALTY PROFESSIONALS, INC
OAKCREST-516 - S5147029 - 7393 GRAND AVE, WINTER PARK, FL 32792 8 Days on yellowkey SHORT SALE
$200,000 | Single Family Home | 3 beds | 2.0 baths | 2 car
Short Sale. Short Sale – Subject to Lender Approval. Exceptional investment opportunity in the desirable Winter Park area. This property offers strong potential for value-add through renovation or repositioning. Located in an established community with no HOA, the home sits on a generously sized lot, providing flexibility for improvements and long-term upside. The current layout presents a solid starting point for updates, making it suitable for rental income, resale, or portfolio expansion. Conveniently positioned near shopping, dining, parks, and major roadways, with access to highly regarded schools and surrounding amenities. Winter Park continues to experience steady demand, supporting long-term investment potential. Property is being sold as-is. Buyer to verify all measurements, condition, and intended use. Don’t miss this opportunity to secure a property with upside in a sought-after Central Florida location. Open House April 15th 9am to noon Highest and Best due April 17th
Listing is courtesy of: DREAM HOME REALTY GROUP AND ASSOCIATES LLC
EASTGATE SUB - O6396498 - 2007 EDWIN BLVD, WINTER PARK, FL 32792 8 Days on yellowkey
$375,000 | Single Family Home | 3 beds | 1.5 baths
Excellent opportunity to build your dream home in Winter Park. 10,278 SqFt corner lot. Value is in the Land, home being sold AS-IS. Zoned for Lakemont, Maitland Middle, Winter Park High. Centrally located near restaurants, shopping, Winter Park Hospital & a short drive to Park Avenue, Rollins College & many local parks. This sale is strictly for the value of the land & location.
WINTER PARK VILLAGE - O6395313 - 2430 CHANTILLY AVE, WINTER PARK, FL 32789 8 Days on yellowkey
$1,665,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar
Nearing completion and set to be move-in ready in just three weeks, this exceptional residence represents one of the best values currently available in Winter Park. This remarkable residence designed by renowned architect Gary Hancock is a masterclass in craftsmanship, architecture, and timeless elegance. From the moment you arrive, the home commands attention with a breathtaking façade defined by graceful archways and refined architectural symmetry. Every exterior line and material selection has been intentionally chosen to create a presence that feels both bold and enduring, setting this residence apart as something truly exceptional. Inside, the home unfolds into a light-filled interior where design and livability coexist seamlessly. Ten-foot ceilings, level 5 drywall, and an abundance of expansive windows allow natural light to pour into every space, illuminating the impeccable finishes and creating an airy, sophisticated atmosphere throughout. Upgraded designer light fixtures add warmth and character, while the open-concept layout is anchored by a stunning living area centered around a refined fireplace, offering a natural gathering space that feels both intimate and grand. Flowing effortlessly from the living room, the dining area opens through elegant doors to the outdoor entertaining spaces, beautifully blending indoor and outdoor living. At the heart of the home, the chefs kitchen is as visually striking as it is thoughtfully designed. Custom cabinetry, sleek quartz countertops, a paneled refrigerator, and a premium induction range, reflect the builders uncompromising commitment to quality, performance, and clean modern design. The primary suite is a private retreat, highlighted by a spa-inspired bath with a freestanding soaking tub, an expansive walk-in shower, and a beautifully designed walk-in closet with direct access to the laundry room for effortless everyday living. Each secondary bedroom continues the theme of elevated design, offering generous proportions, abundant natural light, and elegantly appointed en-suite baths that ensure comfort and privacy for family and guests alike. Outdoors, the home reveals another level of thoughtful craftsmanship. A covered patio with a fully equipped summer kitchen overlooks a sparkling pool and expansive backyard, creating a setting equally suited for quiet evenings or lively gatherings. What truly defines this residence is the extraordinary level of craftsmanship throughout. No detail has been overlooked, no finish treated as an afterthought, and no design decision made without intention. This is a home that feels as impressive in its execution as it does in its presence.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC
URBAN GREEN 12 - O6393725 - 1250 FORMOSA AVE, WINTER PARK, FL 32789 8 Days on yellowkey
$560,000 | Townhouse | 3 beds | 3.5 baths | 2 gar
Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nestled in the highly sought-after Urban Green Community. Built in 2022, this move-in ready residence showcases sleek, contemporary finishes throughout all three levels. Step up to a welcoming covered and pavered front porch, fenced-in front yard, and into a thoughtfully designed layout. The first floor offers a private bedroom with its own walk in closet and ensuite—perfect for guests or a home office. On the second floor, enjoy open-concept living with a bright and airy great room featuring high ceilings, recessed lighting, and seamless access to an oversized balcony through sliding glass doors. The modern kitchen is a showstopper, complete with quartz countertops, stainless steel appliances, a walk-in pantry, white shaker cabinets and a large center island with breakfast bar seating. Upstairs, you'll find two additional bedrooms, including the spacious primary suite with a walk-in closet, double vanity, glass-enclosed shower, and built-in shelving. The third bedroom also includes its own ensuite for added privacy and comfort. Additional highlights include an oversized rear-entry 2-car garage, laundry room, ample storage, and low-maintenance living. Enjoy unbeatable proximity to I-4, Downtown Orlando, Dubsdread Golf Course, Rollins College, Park Avenue, and Winter Park Village—offering endless dining, shopping, and entertainment options. This modern gem offers the best of both worlds: a turnkey home in a central, vibrant location. Don’t miss your chance to own in one of Orlando’s most desirable areas!
Listing is courtesy of: EXP REALTY LLC
CYPRESS RESERVE - O6395836 - 2820 BEAR ISLAND POINTE, WINTER PARK, FL 32792 11 Days on yellowkey
$2,095,000 | Single Family Home | 3 beds | 4.5 baths | 2 gar
Tucked behind the gates of Cypress Reserve, this stunning custom-built lakefront home sits on 110 feet of private waterfront along the serene shores of Bear Gully Lake. Inspired by a featured Southern Living plan and thoughtfully expanded, the home blends timeless architecture with generous, well-appointed living spaces — all framed by panoramic water views, rolling greens, and towering oaks and cypress trees that define the lakefront lifestyle at its finest. Inside, the main level offers a gracious and versatile floor plan with formal living and dining rooms, a family room anchored by an electric fireplace, and a dedicated office or flex space. The spacious kitchen features custom cabinetry, generous prep space, and an adjoining dinette — with plenty of room to add an island — while a large laundry room with extensive cabinetry and a utility sink, plus a half bath, ensure exceptional everyday functionality. The first-floor primary suite is a true sanctuary, offering breathtaking lake views, a spa-inspired en suite with a jetted tub, walk-in shower, a very desirable his and her split bath with abundant counter space and storage, and an oversized walk-in closet complete with built-in shelving and dresser drawers. Upstairs, two oversized bedrooms each enjoy their own private en suite with tub/shower combination, ample closet space, and comfortable proportions. The enormous bonus room above the garage fills with natural light through dormer windows and offers endless possibilities. A walk-in attic provides exceptional storage rarely found in homes of any size. Step out to the covered back porch and take in sweeping panoramic views of Bear Gully Lake — a breathtaking backdrop that shifts beautifully with the light throughout the day - this is Florida lakefront living at its absolute finest. Meander down to your private dock for a morning kayak or a sunset boat ride, then rinse off at the east-facing porch complete with a sink and outdoor shower before heading back inside. The rolling greens, ancient oaks, and towering cypress trees frame the property in natural splendor, and an additional storage room with its own entrance and hurricane shutters ensures everything you need for lake life is right at hand. Set in the gated community of Cypress Reserve with easy access to top private schools including The Geneva School and Trinity Prep, and with convenient proximity to SR-417 for effortless travel to Orlando International Airport and beyond, this is a rare opportunity to own a one-of-a-kind lakefront estate in one of Winter Park's most coveted settings.
Listing is courtesy of: KELLY PRICE & COMPANY LLC
WINDSONG ELIZABETHS WALK 43/81 - O6395638 - 1636 ELIZABETHS WALK, WINTER PARK, FL 32789 11 Days on yellowkey
$2,195,000 | Single Family Home | 4 beds | 4.5 baths | 2 gar
Discover refined living in this stunning custom-built home located in the coveted community of Windsong. Thoughtfully designed and expertly constructed by Goehring & Morgan, this four-bedroom, 4.5 bath residence offers a perfect balance of elegance, comfort and functionality. From the moment you enter, the home impresses with its airy, open-concept design, ideal for both relaxed living and effortless entertaining. The kitchen serves as a focal point, appointed with leathered granite countertops, a generous center island with seating and a seamless connection to the inviting family room, where a gas fireplace adds warmth and charm. Walls of sliding glass doors extend the living space outdoors to a beautifully designed lanai, complete with a gas-heated pool and a fully equipped summer kitchen featuring a grill, sink, beverage refrigerator and additional seating area. The main level also includes a well-appointed guest suite with a private bath, offering comfort and privacy for visitors, along with a dedicated office or study space. Upstairs, a spacious bonus room provides flexibility for a media room, playroom or lounge, while two additional bedrooms accompany the expansive primary suite. The primary retreat is designed for relaxation, showcasing dual walk-in closets and a luxurious bath with a freestanding soaking tub, oversized shower and separate vanities. High-end finishes are showcased throughout, including travertine flooring across the main living areas and rich wood floors that continue through the bedrooms, staircase, upper hallway and bonus room. As a resident of Windsong, you’ll enjoy access to exceptional community amenities, including resort-style pools, a splash pad, playground and access to the scenic Winter Park Chain of Lakes, creating a lifestyle that is both vibrant and serene in one of Central Florida’s most desirable settings.
CORTLAND PARK - O6395137 - 250 CORTLAND AVE, WINTER PARK, FL 32789 11 Days on yellowkey
$950,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
One or more photo(s) has been virtually staged. Introducing 250 Cortland Ave — a refined expression of Winter Park living, ideally positioned on one of the area’s most picturesque brick-lined streets, surrounded by established luxury homes and mature canopy trees. From the moment you arrive, the home exudes a quiet sophistication, with manicured, low-maintenance landscaping and a sense of privacy that carries throughout the property. An oversized two-car garage and thoughtfully designed exterior set the tone for what awaits inside. Step through the entry and into a light-filled interior where volume ceilings and an open-concept layout create an immediate sense of space and flow. The home is designed to draw your eye outward — through expansive living areas, beyond the enclosed lanai, and into the serene pool and spa, creating a seamless connection between indoor and outdoor living. Every detail has been carefully curated to balance warmth and modern refinement. Rich Brazilian rosewood flooring anchors the main living spaces, while durable quarry tile provides both style and functionality in the kitchen and transitional areas. The kitchen itself has been reimagined with updated cabinetry and modern appliances, offering a clean, sophisticated space that remains highly functional for everyday living and entertaining. The split floor plan provides both comfort and privacy, with a spacious primary suite and well-appointed secondary bedrooms. Both bathrooms have been tastefully updated with contemporary finishes, while additional enhancements throughout the home — including updated lighting, hardware, flooring, and fresh interior touches — contribute to its move-in-ready appeal. Designed for the Florida lifestyle, the home truly comes to life when the expansive sliding glass doors are opened, blending the interior with the screened outdoor living space. The pool and spa become a natural extension of the home — perfect for quiet mornings, entertaining guests, or simply enjoying the year-round sunshine in complete privacy. Located just moments from Lake Mizell, part of the highly sought-after Winter Park Chain of Lakes, the property offers not only a beautiful home, but a lifestyle defined by scenic surroundings, walkability, and timeless charm. 250 Cortland Ave is more than a home — it is a rare opportunity to own a thoughtfully designed residence in one of Winter Park’s most desirable and established neighborhoods.
Listing is courtesy of: CREEGAN GROUP
KAROLINA ON KILLARNEY - O6391469 - 1870 STAUNTON AVE, WINTER PARK, FL 32789 11 Days on yellowkey
$1,250,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction, MJS Designers, and Collins & Co. From concept to completion, every detail is thoughtfully orchestrated, allowing the future owner to tailor finishes, layout, and architectural style to match their vision. Ideally positioned just minutes from Park Avenue’s renowned dining, boutique shopping, and vibrant lifestyle, the property also offers convenient access to I-4, College Park, and Downtown Orlando—delivering both prestige and connectivity. The proposed residence spans approximately 2,500 square feet and is designed with intentional flow, abundant natural light, and refined modern finishes. The layout allows for elevated indoor-outdoor living, with the option to incorporate a private pool and outdoor entertaining space. Located within close proximity to major medical centers, including AdventHealth Winter Park (approximately 2.5 miles), AdventHealth Orlando (approximately 4 miles), and Orlando Health Orlando Regional Medical Center (approximately 5 miles), this location offers both lifestyle and practical convenience for medical professionals and those seeking proximity to top-tier healthcare. Opportunities like this are increasingly limited in Winter Park—secure your homesite and begin designing a one-of-a-kind residence in one of Central Florida’s most desirable zip codes.
ORWIN MANOR WESTMINSTER SEC - O6384358 - 1651 WESTCHESTER AVE, WINTER PARK, FL 32789 11 Days on yellowkey
$1,449,000 | Single Family Home | 3 beds | 2.5 baths | 1 gar
One or more photo(s) has been virtually staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome you into the main living space, while the showpiece kitchen delivers true chef-level design with new Custom European Cabinetry, Quartz Countertops with a Waterfall Island, Porcelain Tile floors, premium lighting, under counter Kitchen Aid Ice Maker and a top-tier appliance suite including Wolf Gas Range-top, Wolf Built-in Oven & Microwave and Bosch Refrigerator and Dishwasher. The primary suite is a serene retreat with a newly redesigned spa style bath with frameless walk-in shower, soaking tub, new double sink vanity and lighting—plus a walk-in closet with California Closet built-in’s and a versatile bonus room ideal for a sitting area, nursery, or dedicated laundry space. Outdoors, enjoy resort-style living under the expansive 26’ x 24’ covered Lanai featuring vaulted tongue-and-groove ceilings, tile flooring, a striking stone gas fireplace with RealFyre burners, stainless mantle, perfect for effortless entertaining. There is even enough room to customize the outdoor space with your own Pool Oasis. Recent improvements include a re-roof 2020, HVAC System, Double-Pane windows, 4-panel slider & front door, fresh interior/exterior paint, new custom shades, privacy bamboo landscaping, privacy fencing and an extended paver driveway. The attached Garage offers dedicated storage space and a bonus room with mini-split system which could offer space for home gym or office. Just minutes from Park Avenue’s acclaimed dining and shopping, top Winter Park amenities, Advent Health Medical Campus and quick access to key corridors for an easy downtown Orlando commute, this is 32789 living at its most refined—classic architecture, modern systems, and elevated indoor-outdoor lifestyle in one of Winter Park’s most sought-after neighborhoods.
Listing is courtesy of: SERHANT