Winter Park, Orlando, FL Real Estate | Winter Park, Orlando, FL 2 Bathroom Properties for Sale

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Welcome home to this charming 1940's bungalow in Orwin Manor, one of Winter Park’s most sought-after neighborhoods. The single-story home has 3 bedrooms, 2 full baths and 1,594 square feet of living space. It keeps its original character, with wood floors throughout and graceful curved entryways. In the living room, a wood-burning fireplace sets a warm, inviting tone, and the open layout flows into the formal dining room, making the home easy to entertain in and comfortable for everyday living. The kitchen has been updated with shaker cabinetry, granite countertops and stainless steel appliances, while keeping the home’s vintage charm. A split bedroom plan gives the primary suite added privacy, with an en suite bath featuring a walk-in shower and a walk-in closet. Outside, the home sits on an oversized 0.31-acre lot (100 x 135), leaving plenty of room for gardening, play, outdoor living or future expansion, and a detached one-car garage adds storage and parking. Orwin Manor is a well-established, walkable community close to Winter Park’s restaurants and shopping, with easy access to major roadways. This home has great bones and a prime location, with plenty of potential to make it your own. Opportunities like this in Orwin Manor don’t come along often, so schedule your private showing today!

1401 Pelham Road, Winter Park

$699,900

3 Beds ⋅ 2 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code

Enjoy bright, inviting living and your own screened pool retreat in Winter Park! This 3-bedroom, 2-bath home offers 1,666 square feet with vaulted ceilings, abundant natural light, and plantation shutters. The spacious family room features laminate flooring and a wood-burning fireplace, creating a welcoming place to gather. The updated kitchen offers stainless steel appliances, ample drawer storage, a pullout pantry, and a sunny dinette with sliding doors to the outdoor living area. Multiple access points throughout the home connect to the screened pool enclosure, where a recently resurfaced pool and covered patio provide space for relaxing and entertaining. The primary suite features a walk-in closet and an en-suite bath with dual sinks and a separate shower. Two additional bedrooms offer flexibility for guests or a home office, while the second full bath includes a bathtub. An attached two-car garage provides laundry space, extensive cabinetry, and pull-down attic access. All appliances are included, adding convenience to this inviting Winter Park home.

1884 Jessica Court, Winter Park

$320,000

3 Beds ⋅ 2 Baths ⋅ Winter Park Oaks SubDv. ⋅ 32789 Zip Code

Virtually Staged. Winter Park living, without the Winter Park price tag! This 3 bed, 2 bath block home has already done the big stuff for you: 2020 roof, 2020 HVAC, 2023 water heater, and updated plumbing. That means your weekends are for enjoying life where you call home. Fresh paint inside and out sets the tone the moment you pull up. Step inside to a bright, open floor plan where the kitchen, dining, and living spaces flow together for easy weeknight dinners and lazy Saturday mornings. The kitchen and bathrooms have been updated with a clean, modern feel, so all that’s left is to unpack. Out back, a fully fenced vinyl yard gives you privacy and room to play, garden, or host the cookout. A one-car garage adds plenty of storage. And the location? It’s hard to beat. You’re minutes from everything Winter Park has to offer, tucked right behind the new LifeTime fitness club, with exciting new development planned for the area. Homes this updated in this location don’t come around often. Schedule your showing today!

148 Oak Grove Rd, Winter Park

$575,000

3 Beds ⋅ 2 Baths ⋅ Galloway Place Rep SubDv. ⋅ 32789 Zip Code

Charming 1948 home with Winter Park Chain of Lakes access offers a great opportunity for buyers looking to renovate or explore new construction in an established Winter Park location. Conveniently located near Rollins College, Park Avenue, and Winter Park Hospital, with access to Lake Osceola just a short walk away to launch a paddleboard or canoe. The 3-bedroom, 2-bath character home offers a split floor plan with original hardwood floors, arched doorways, plantation shutters, and a formal living room with a gas fireplace and built-ins. The updated kitchen features Carrara quartz countertops, stainless appliances, and wood cabinetry, and opens to the dining and sunrooms. French doors from the sunroom lead to a covered patio and backyard with mature landscaping, paver walkways, and a tranquil cabana perfect for relaxing. Additional features include an attached one-car garage with washer/dryer, walk-in closets, and a circular driveway for additional parking. Improvements include new PEX water supply lines (2025) and partial drain-line replacement, recent interior painting, and updated bathrooms with a 2019 renovation featuring marble shower and floors. With its original character, thoughtful improvements, and convenient Winter Park location, this home offers an opportunity for its next owner to make it their own.

1399 Aloma Avenue, Winter Park

$950,000

2 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster SubDv. ⋅ 32789 Zip Code

Experience the charm of Winter Park living in this beautifully renovated Orwin Manor residence, where more than $41,000 in luxurious upgrades complement timeless character, sophisticated interiors and exceptional outdoor living in one of the area’s most desirable settings. Nestled along a tree-lined street and surrounded by mature landscaping, this 1,947-square-foot home offers two bedrooms, two baths and a versatile floor plan that can be easily converted back to its original three-bedroom configuration, providing flexibility for a home office, guest room or additional bedroom. Inside, rich hardwood flooring, crown molding, plantation shutters and a wood-burning fireplace lend warmth and character to the home, while French doors and abundant windows invite natural light throughout. The kitchen serves as an elegant centerpiece with custom cabinetry, Carrara marble countertops, a gas range and oven, stainless steel appliances, a breakfast bar and generous workspace. A tankless water heater adds modern efficiency and convenience. Multiple living and dining areas create an effortless flow for entertaining, while the expansive primary suite offers a private retreat with ample space for a sitting area. Beyond the interiors, the backyard creates a private resort-style setting rarely found so close to the heart of Winter Park. Fresh landscaping surrounds a saltwater pool, putting green, and expansive paver patio. A covered outdoor living and dining area provides an inviting backdrop for year-round entertaining. Mature trees, manicured hedges and multiple seating areas enhance the sense of privacy, creating a serene escape equally suited for quiet mornings, afternoons by the pool and evenings with guests. A paver driveway and charming covered entry complement the home’s classic architecture, while a Tesla charger adds the convenience of at-home EV charging. Ideally positioned in Orwin Manor, the residence is just minutes from I-4 access and AdventHealth, with convenient proximity to Park Avenue’s renowned boutiques, dining and cafés, as well as College Park and Downtown Orlando. Zoned for Killarney Elementary School, College Park Middle School and Edgewater High School, this distinctive residence presents an exceptional opportunity to enjoy the best of the Winter Park lifestyle.

1411 Devon Road, Winter Park

700 Melrose Avenue Unit M23, Winter Park

$354,000

2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

Virtually Staged. Winter Park living, with a view you’ll actually want to come home to! This spacious 2-bedroom, 2-bath condo at Winter Park Gardens is clean and puts you in the middle of it all while giving you a peaceful place to escape. Set on the second floor with elevator access, the home overlooks the community pool and lush mature gardens, giving the living spaces a beautiful green backdrop. Step inside, to your open living area, flooded with natural light. The Florida room adds an extra spot to relax with a good book, work from home, or enjoy your morning coffee, with updated windows bringing in plenty of natural light while helping to keep cooling costs low. Fresh interior paint gives the home a clean, updated feel and an easy canvas for your own style. Just outside your door, Winter Park Gardens offers beautifully landscaped grounds, a community pool, pond, and lighted walking paths. Then there's the location. Walk or bike ride to Park Avenue's restaurants, shopping, and boutiques, the Winter Park Tennis Center, Rollins College, and Mead Botanical Garden. This is a great opportunity to enjoy the lock and go Winter Park lifestyle without giving up space, convenience, or a little peace and quiet. Call to schedule your showing today!

700 Melrose Avenue Unit M23, Winter Park

$255,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Enjoy peaceful lake views from this charming second-floor, 2-bedroom, 2-bathroom condo in the desirable Chateaux Du Lac community in Winter Park! This inviting residence offers a functional layout filled with natural light and tranquil water views. Residents enjoy a variety of community amenities, including a swimming pool, clubhouse, sauna, and boat ramp access. Ideally situated in the heart of Winter Park, this community offers a walkable lifestyle with convenient access to shopping, dining, and entertainment, just minutes from the charming boutiques and restaurants of Park Avenue. Whether you're seeking a primary residence or seasonal retreat, this condo offers the perfect combination of location, convenience, and lakeside living. Experience the best of the Winter Park lifestyle!

1500 Gay Road Unit 26-C, Winter Park

$325,000

3 Beds ⋅ 2 Baths ⋅ Fairview Heights Rep SubDv. ⋅ 32789 Zip Code

Welcome to 310 Granada Drive, an excellent opportunity to own a single-family home in the highly desirable Winter Park 32789 area. Situated in the established Fairview Heights community, this 3-bedroom, 2-bath concrete-block home offers 1,344 square feet of living space with a functional single-story floor plan and plenty of potential for a buyer looking to make a home their own. Inside, the home features tile flooring throughout the main living and dining areas, vaulted ceilings, ceiling fans, and a split-bedroom layout that provides added separation and flexibility. The kitchen is equipped with a convection oven, dishwasher, microwave, and refrigerator, while indoor washer and dryer hookups add everyday convenience. Step outside through the covered rear entry to a brick-paver patio overlooking the fully fenced backyard. Mature trees provide natural shade, while the outdoor space offers plenty of room for entertaining, gardening, pets, or simply enjoying the Florida lifestyle. A one-car carport provides covered parking, and the property is connected to public water and sewer. One of the property's biggest advantages is its Winter Park location. Enjoy convenient access to shopping, restaurants, parks, major roadways, downtown Winter Park, Park Avenue, College Park, and surrounding Orlando destinations while still coming home to an established residential neighborhood. With NO HOA, solid concrete-block construction, a fenced yard, and a sought-after 32789 address, 310 Granada Drive presents an exciting opportunity for an owner-occupant, investor, or buyer looking to renovate and add their personal style. Schedule your private showing and discover the possibilities this Winter Park property has to offer!

310 Granada Drive, Winter Park

100 S Interlachen Avenue Unit 401, Winter Park

$850,000

3 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Opportunity knocks at The Cloisters! This rarely available fourth-floor corner residence offers an exceptional opportunity to create a truly personalized home, with windows on four sides filling the interiors with abundant natural light and capturing desirable eastern exposures, perfect for viewing the sunrise and rocket launches. Also, enjoy tree top and lake views. Held by the same family since 1979, this residence offers more than 1,600 square feet of living space, this 3 bedroom - 2 bath unit is ready for its next chapter. While the interiors await updating, the generous floor plan provides a wonderful blank canvas with endless possibilities to reimagine the space and make it your own. Additional features include in-unit washer and dryer hookups, an assigned parking and storage closet and the unique privacy afforded by its corner location. Nestled along the shores of beautiful Lake Osceola, The Cloisters offers an exceptional lifestyle with an array of desirable amenities, including a sparkling swimming pool, boat slips, a private dock, two fitness rooms, a clubhouse, internet and cable, an on-site manager, and an outdoor grilling area. Ideally situated in the heart of Winter Park, this sought-after community is just a short stroll from The Alfond Inn, SunRail, and the charm of Park Avenue, where you can enjoy an inviting collection of sidewalk cafés, fine dining, boutique shopping, and the picturesque beauty of Central Park. Experience the best of Winter Park living in this exceptional lakefront community. Bring your designer, your vision, and your personal style to transform this special Cloisters residence into something extraordinary. Call today for your private viewing of this wonderful unit.

100 S Interlachen Avenue Unit 401, Winter Park

1250 S Denning Drive Unit 119, Winter Park

$265,000

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

Virtually Staged. Welcome to easy, low-maintenance living in the heart of Winter Park! This beautifully updated 2-bedroom, 2-full-bath, first-floor corner residence at Mead Garden Condominiums offers a fresh, move-in-ready interior paired with an exceptional location just minutes from some of Winter Park’s most desirable destinations. Recent updates include new luxury vinyl flooring throughout the kitchen and great room, new carpeting in both bedrooms, fresh interior paint, and a recently redone screened-in porch with a refreshed frame and new screening. The thoughtfully updated kitchen features shaker-style cabinetry, granite countertops with breakfast bar, and stainless steel appliances. Additional features include remodeled bathrooms, low-Emissivity windows and sliding glass door, crown molding, updated baseboards and light fixtures, Nest thermostat, A/C replaced in 2018, and water heater replaced in 2019. Enjoy Florida living from the screened-in porch with convenient direct access to the community pool, onsite laundry facility, and mailroom. The first-floor corner location offers added privacy, comfortable single-level living, and a designated parking space.

1250 S Denning Drive Unit 119, Winter Park

$479,900

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Don’t miss this wonderful opportunity to own a 3-bedroom, 2-bath home in the desirable Orwin Manor area of Winter Park, conveniently located just minutes from AdventHealth, Park Avenue, Downtown Orlando, and I-4. This spacious two-story home features a flexible layout with a two-car garage, remodeled bathrooms, and plenty of living space. The first floor offers a large bedroom, a beautifully remodeled full bathroom, a laundry area and access to the enclosed/screened patio and backyard. Upstairs, you’ll find an open kitchen with stainless steel appliances, a dining area, and a spacious living room. The second floor also features two bedrooms, including the primary bedroom with a remodeled bathroom. Wood flooring and carpet are featured throughout the home. Additional improvements include a roof approximately 5 years old, completely refreshed landscaping and outside power washed. Sliding doors off the kitchen and dining area lead to a new outdoor deck, creating an ideal space for outdoor dining, entertaining, and enjoying the Florida lifestyle. The convenient location provides easy access to major roads, shopping, dining, entertainment, and all that Winter Park and Downtown Orlando have to offer. This home offers a great combination of location, space, and recent updates. Schedule your showing today!

1660 Orange Avenue, Winter Park

1602 Alabama Drive Unit 107, Winter Park

$1,150,000

2 Beds ⋅ 2 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code

Experience timeless lakefront living at The Alabama, one of Winter Park’s most distinctive and treasured residences. Set on more than five gated acres along the Winter Park Chain of Lakes, this beautifully appointed 2-bedroom, 2-bath condominium offers an exceptional blend of elegance, privacy and effortless living. Inside, soaring 11-foot ceilings and 7.5-inch plank white oak flooring create a light and refined atmosphere. The beautifully designed kitchen features Viking and Fisher & Paykel appliances, marble countertops and generous cabinetry, flowing seamlessly into the great room where expansive windows frame picturesque views of Lake Maitland. The serene primary suite is a private retreat with lake views, custom closet built-ins and an elegant marble bath. The guest suite opens to an extraordinary 400-square-foot private terrace with gated access—one of only five private patios within the community. It is an exceptional setting for morning coffee, intimate entertaining or simply enjoying the lush surroundings. Residents enjoy beautifully manicured grounds, a sparkling pool, fitness center and clubhouse, along with an on-site manager, climate-controlled storage, bike and scooter storage, ample guest parking and one deeded covered parking space. A new roof was completed in 2026, and boat slips are available on a first-come, first-served basis. Small pets are welcome; rentals are not permitted. From morning coffee overlooking the lake to spectacular sunsets over Lake Maitland, this is a rare opportunity to experience the beauty, history and understated elegance of lakefront living in Winter Park.

1602 Alabama Drive Unit 107, Winter Park

$1,250,000

3 Beds ⋅ 2 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

SPECTACULAR OPPORTUNITY ON SCENIC LAKE KILLARNEY Discover a rare opportunity to live on scenic Lake Killarney—a 236-acre, spring-fed private lake with no public access. Nestled along a charming, tree-canopied, lakefront dead end brick street, this 1947 bungalow offers 1,747 square feet of pure potential, featuring 3 bedrooms, 2 baths, a 2-car garage, and a lovely corner lot. Renovate the existing home or create your dream residence in this tranquil setting, where breathtaking sunsets and peaceful lake views await. Enjoy the convenience of being within walking distance of restaurants and shopping, while having easy access to Interstate 4, Rollins College, and all that Winter Park’s renowned Park Avenue has to offer. THREE UNIQUE OPPORTUNITIES: Option 1 — $1,250,000 115' x 65' property + 65' lakefront. Option 2 — $1,450,000 155' x 65' property + 65' lakefront. Option 3 — $2,250,000 155' x 95' property + 95' lakefront. A truly rare find in a quaint and desirable neighborhood, offering the flexibility to renovate, expand, or build the home you’ve always envisioned. Come experience the tranquility, privacy, and beauty of Lake Killarney. WELCOME HOME!

120 Broadview Avenue, Winter Park

250 Carolina Avenue Unit 202, Winter Park

$649,000

3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

Welcome to Park West, an exclusive gated community ideally located just moments from the heart of downtown Winter Park. This impeccably maintained 3-bedroom, 2-bath residence offers a spacious and thoughtfully designed floor plan. The inviting living and dining areas feature an open-concept layout anchored by a traditional decorative fireplace, creating a warm and comfortable setting for both everyday living and entertaining. The generous primary suite offers a private en-suite bath with a walk-in shower and an expansive walk-in closet. The second bedroom is conveniently positioned near the hall bath, which features a tub/shower combination. A dedicated laundry room with built-in shelving and abundant storage adds a level of convenience rarely found in condominium living. Residents of Park West enjoy an array of amenities, including a clubhouse, resort-style swimming pool, and tennis court which also has lines for pickleball, all within a beautifully maintained gated setting. Perhaps the greatest luxury is the location. From Park West, it’s an easy stroll to the boutiques, restaurants, and cultural attractions of Park Avenue, as well as Central Park, world-class museums, the SunRail station, and the Winter Park Golf Course. Offering space, comfort, amenities, and an unbeatable location, this is a wonderful opportunity to own a residence in one of Winter Park’s most desirable communities.

250 Carolina Avenue Unit 202, Winter Park

$950,000

3 Beds ⋅ 2 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

913 Moss Lane is in the Vias of Winter Park, on a tree-lined street in Maitland Shores. Neighborhood access to the Winter Park chain of lakes is a block away. Winter Park Racquet Club is a short walk. Park Avenue is a short drive. The home is zoned for Dommerich Elementary, Maitland Middle, and Winter Park High. The house is a 1953 split-level with 3 bedrooms, 2 baths, about 1,887 square feet, and a two-car garage. The main floor has the living room, dining area, kitchen, and Florida room. The bedrooms are upstairs. The 2023 renovation added new flooring, interior and exterior paint, a kitchen with white cabinetry, stone counters, and stainless appliances, and an updated bath with a walk-in glass shower. The backyard is fenced and has a patio. There is no homeowners association. This is a renovated three-bedroom in the Vias. See it for the street, the schools, and the lakes.

913 Moss Lane, Winter Park

$3,950,000

4 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Rare Winter Park redevelopment opportunity on a NEARLY HALF-ACRE CORNER PARCEL JUST MINUTES FROM PARK AVENUE. Newly priced at $3,950,000, this R-3 ZONED (Medium-Density Residential) property offers outstanding redevelopment potential, INCLUDING CAPACITY FOR UP TO SEVEN RESIDENTIAL UNITS. Ideally positioned between Park Avenue and Winter Park Village, the property offers convenient access to renowned dining and shopping, Rollins College, cultural attractions, AdventHealth Winter Park, and major transportation corridors. Three existing residences occupy the site and contribute no value to the offering. Properties of this size and zoning, so close to Park Avenue, are exceptionally rare. THIS PROPERTY IS CROSS-LISTED AS VACANT LAND WITH THE MLS #O6431538.

540 N Pennsylvania Avenue, Winter Park

1250 S Denning Drive Unit 127, Winter Park

$245,000

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

Virtually Staged. Updated two-bedroom, two-bath residence offering 908 square feet and a first-floor, pool-facing location in Mead Garden Condominium. The move-in-ready interior features luxury vinyl plank flooring throughout the living areas and bedrooms, tile flooring in the baths and defined living and dining spaces. The kitchen is appointed with white transitional cabinetry, granite countertops, a white subway tile backsplash and stainless steel appliances, including a refrigerator, range, microwave and dishwasher. A pass-through to the dining area incorporates built-in cabinetry, glass-front display storage and additional counter space. The dining area flows into the living room, where sliding glass doors open to a screened-in porch overlooking the community pool and landscaped grounds. The primary bedroom features natural light from a pool-facing window, built-in closet storage and an en-suite bath with a walk-in shower and white tile surround. A second bedroom provides flexible space for a variety of uses, while the second full bath offers a tub and shower combination. Additional features include a newer water heater, updated plumbing fixtures and convenient access to the community laundry room just outside the residence. From 1250 South Denning Drive, Residence 127 offers proximity to Mead Botanical Garden, Rollins College, Park Avenue, Azalea Park, Seven Oaks Park and Winter Park dining and retail.

1250 S Denning Drive Unit 127, Winter Park

$699,000

3 Beds ⋅ 2 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code

Tucked beneath mature oak trees, 1850 Bryan Avenue is a well-maintained home offering comfortable single-story living in Winter Park. Natural light and warm wood floors flow through the inviting living and dining spaces, while a flexible bonus room is well suited for a home office, den or creative space. The kitchen features wood cabinetry and ample counter space. The spacious primary suite offers a private retreat. Additional features include an indoor laundry room and an attached two-car garage. Outside, the fenced yard provides a peaceful setting for gardening, entertaining or relaxing beneath the trees. With shopping, dining, parks and other Winter Park amenities nearby, this home brings together character, comfort and a desirable location.

1850 Bryan Avenue, Winter Park

$950,000

3 Beds ⋅ 2 Baths ⋅ Lake Maitland SubDv. ⋅ 32789 Zip Code

A RARE WINTER PARK RENOVATION OPPORTUNITY DIRECTLY ACROSS FROM HOWELL BRANCH PRESERVE! Situated on an approximately 0.23-acre lot, this distinctive 3-bedroom, 2-bath home offers an exceptional opportunity for an investor, renovator, or buyer seeking to complete and personalize a property in one of Central Florida’s most desirable communities. Renovations have already begun, providing the next owner with a valuable head start. The home features a spacious open-concept living, dining, and kitchen area; original hardwood flooring in several bedrooms; updated flooring in other areas; renovated bathroom elements; a large walk-in shower; generous flex and storage space; and an expansive driveway and garage area. Some improvements and finish work remain, allowing the buyer to complete the renovation according to their own vision. The approximately 10,219-square-foot lot is directly across from the 10.38-acre Howell Branch Preserve, which offers a playground, fitness trail with exercise stations, picnic pavilion, boardwalk, observation deck, restrooms, open lawn, and protected natural surroundings. Property is offered strictly AS IS. Public records reflect approximately 1,487 square feet of heated living area. Additional areas, measurements, permitted improvements, and intended uses must be independently verified by the buyer. The seller will not complete repairs. Bring your contractor and imagination to explore the possibilities offered by this unique Winter Park property.

1220 Howell Branch Road, Winter Park

311 E Morse Boulevard Unit 4-5, Winter Park

$925,000

2 Beds ⋅ 2 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Experience the best of downtown Winter Park living at Whispering Waters, a desirable 55+ lakefront community ideally located on beautiful Lake Osceola and just a short stroll from iconic Park Avenue. Priced BELOW APPRAISED VALUE, this rare third-floor mid-century modern condo combines an unbeatable location, spacious living, and an easy, low-maintenance lifestyle. Step inside to a bright, inviting interior filled with natural light from multiple floor-to-ceiling windows. The spacious living and dining areas overlook tranquil waterfall ponds and beautifully landscaped grounds, creating a peaceful retreat in the heart of Winter Park. A versatile bonus space is perfect for a home office, den, reading room, or creative space. The expansive owner’s suite offers a private sitting area, dual closets, pool access, and a spacious bath with a relaxing jetted tub. The generously sized secondary bedroom features its own cozy reading nook and dual closets—ideal for guests or additional living space. Convenience is built right in with private in-unit washer and dryer hookups, secure underground parking with a deeded space, and elevator access. Even better, the monthly association DUES INCLUDE ELECTRIC, WATER, GAS, SEWER & TRASH, helping make everyday living refreshingly simple. Residents also enjoy an on-site property manager, additional laundry facilities, a community clubhouse, sparkling pool, and beautiful lakefront surroundings. Leave the car at home and enjoy the boutiques, cafés, restaurants, museums, and events of Park Avenue, stroll through Central Park, catch the SunRail or Amtrak, or enjoy nearby Rollins College and Winter Park’s highly rated public golf course. With its PRIME LAKEFRONT SETTING, WALKABLE PARK AVENUE LOCATION, UTILITIES INCLUDED & LOW-MAINTENANCE LIFESTYLE, this condo offers a RARE OPPORTUNITY to enjoy one of Central Florida’s most sought-after communities. COME DISCOVER THE LIFESTYLE THAT MAKES WHISPERING WATERS AND WINTER PARK SO SPECIAL—schedule your private showing today.

311 E Morse Boulevard Unit 4-5, Winter Park

250 Carolina Avenue Unit 205, Winter Park

$739,000

2 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

Discover the ease of Winter Park living in the highly desirable gated community of Park West, ideally located just steps from Park Avenue. From this exceptional location, charming boutiques, sidewalk cafés, award-winning restaurants, and the popular weekly farmers market are all within easy reach—giving you the freedom to leave the car behind and enjoy everything Park Avenue has to offer. This beautifully remodeled second-floor corner residence offers the privacy, comfort, and convenience you've been looking for. The thoughtfully updated kitchen features wood cabinetry and granite countertops, while both bathrooms have been tastefully remodeled. Spacious bedrooms, generous storage, and a comfortable flow throughout the home provide plenty of room for everyday living or welcoming guests. Enjoy the simplicity of a well-maintained community with beautifully landscaped grounds, a sparkling swimming pool, and tennis courts. As a corner unit, this residence also offers enhanced privacy and convenient access into and out of the building—perfect for those seeking a low-maintenance lifestyle or an easy lock-and-leave retreat. With Rollins College and Full Sail University nearby and Park Avenue just moments away, this condo puts the best of Winter Park right at your doorstep. Whether you're looking for a full-time residence, a seasonal escape, or simply a home that allows you to spend less time on maintenance and more time enjoying life, Park West offers an exceptional combination of location, comfort, and convenience.

250 Carolina Avenue Unit 205, Winter Park

$469,000

4 Beds ⋅ 2 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code

Income Producing Duplex in Winter Park, Florida! Great investment opportunity in a desirable location! This duplex features two 2-bedroom, 1-bath units, each approximately 600 square feet, with private entrances, central AC, and a private screened patio area. Both units are currently leased, providing established rental income and long-term occupancy. Each unit offers a spacious living area and a functional kitchen, with a shared laundry room equipped with a washer and dryer for added convenience. Both units include a full bath with updated showers. Enjoy all of Downtown Winter Park, including the shops and restaurants along Park Avenue, Winter Park Village, and an abundance of entertainment and recreational options such as Mead Botanical Garden, Winter Park Tennis Center, Winter Park Golf Course, and much more. The property also offers easy access to major highways and is just minutes from Rollins College. Don't miss this opportunity to own an income-producing property in one of Central Florida's most desirable areas with no HOA. Pictures were taken prior to occupancy.

2183 Crandon Avenue, Winter Park

$405,000

3 Beds ⋅ 2 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code

Nestled in Winter Park's Lake Bell Terrace neighborhood, this 3 bedroom, 2 bathroom home is located close to everything that makes Winter Park special, Park Avenue's shops and restaurants, Winter Park Village, Mead Botanical Garden, the Winter Park golf course, and more. Inside, an open, light-filled living area flows effortlessly into the kitchen and dining room, with wood and tile flooring throughout. A large bonus room adds flexible space for a home office, playroom, or media room, while the spacious bedrooms and abundant storage make everyday living easy. Outside, a classic front porch invites cozy mornings with coffee, a screened patio provides year-round outdoor living, and the beautiful backyard with additional open patio is perfect for grilling and gathering. A dedicated laundry/utility room and attached 1 car garage complete this Winter Park gem.

1955 Eland Avenue, Winter Park

$799,999

2 Beds ⋅ 2 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully maintained 1960s home nestled in one of Winter Park’s desirable neighborhoods, where classic charm meets thoughtful modern updates. Set along picturesque brick streets shaded by mature trees, this inviting home offers a warm, light-filled interior and a private backyard oasis. From the moment you enter, you’ll notice the abundance of natural light and the large windows that frame the living spaces. The spacious living room flows seamlessly into a bright, functional kitchen featuring newer appliances and a large window overlooking the front yard. Just off the kitchen, an indoor laundry room adds everyday convenience. A beautiful sunroom overlooks the private, landscaped backyard and offers a versatile space that could easily serve as a home office, reading room, or additional sitting area. Down the hallway, the spacious primary suite features an en-suite bathroom, ample closet space, and abundant natural light with peaceful views of the backyard. The second bedroom is generously sized and includes a walk-in closet. Step outside to discover a true gardener’s paradise. The lush, private backyard features a beautiful paved patio, winding paved pathway, mature landscaping, and plenty of space to relax, entertain, or enjoy the outdoors. The location is hard to beat, walking distance to the beautiful Lake Knowles and Lake Wilbar, just minutes from Park Avenue, the Winter Park YMCA, AdventHealth Winter Park, Rollins College, the Winter Park Chain of Lakes, golf courses, and an abundance of exceptional dining and shopping. The home also offers access to top-rated Orange County schools. Important updates include a complete remodel and added square footage (2009), a newer roof (2022), regularly maintained HVAC system (2020), hot water heater (2024), updated bathrooms (2025), kitchen appliance updates (2026), and a regularly maintained irrigation system. This special home offers the perfect blend of classic Winter Park character, modern updates, beautiful outdoor living, and an unbeatable location.

1431 Palm Avenue, Winter Park

1250 S Denning Dr Unit Unit 233, Winter Park

$242,500

2 Beds ⋅ 2 Baths ⋅ Mead Garden Condominium SubDv. ⋅ 32789 Zip Code

Located just minutes from Winter Park's famed Park Avenue, this charming 2 bed, 2 bathroom corner condominium features a light and bright open floor plan, updated finishes, views of Mead Gardens, and one of Central Florida's most sought after locations! As you enter the front door, you are immediately welcomed by views of Mead Botanical Gardens, Khaki oak wood-look luxury vinyl floors, an open living/dining room combo, a private balcony with garden views and kitchen with freshly painted cabinets and stainless steel appliances. Off of the family room, 2 spacious bedrooms including a master suite with a renovated bathroom, and a second bedroom with private access. Everyday is a vacation when you can start your day off with a coffee on the private balcony, cool off on a warm summer's day in the pool and end it with a walk through the 48 acre natural enclave just next door as the sun sets. Zoned for A rated schools including Audobon Park and Winter Park High school and located just minutes from world class shopping, dining and entertainment in historic downtown Winter Park, Downtown Orlando, and College Park. Schedule your showing Today!

1250 S Denning Dr Unit Unit 233, Winter Park

$429,000

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

A rare opportunity in Winter Park's 32789: one of the most affordable single-family homes currently on the market! Charming 1950 block bungalow in sought-after Orwin Manor! This inviting 3-bedroom, 2-bath home sits on a generous corner lot with a side-load driveway and garage, offering added breathing room, curb appeal, and convenience. A paver walkway leads to the covered front porch, setting the tone for the home’s classic character and welcoming appeal. Inside, original hardwood floors complement a renovated, generously sized kitchen—ideal for everyday living and entertaining. Recent improvements include a 2020 roof, 2021 HVAC system, plus new windows, doors, and added insulation. The dining room features French doors opening to a newly poured concrete patio and charming backyard offering loads of potential for gardening, play, pets, or creating your own private outdoor retreat. Previously utilized as an investment rental, this property presents an excellent opportunity for an owner-occupant or investor seeking a desirable Winter Park location with strong rental appeal. Enjoy close proximity to AdventHealth’s world-class Orlando campus, as well as the shopping, dining, and lifestyle destinations of Winter Park, Park Avenue, Mills 50, and downtown Orlando. A wonderful opportunity to own a character-filled home in one of the area’s most desirable central neighborhoods.

1652 Berkshire Avenue, Winter Park

$499,900

3 Beds ⋅ 2 Baths ⋅ Flamingo Shores SubDv. ⋅ 32789 Zip Code

Welcome to your ideal single-story retreat in the heart of Winter Park's highly desirable Flamingo Shores neighborhood in zip 32789. This classic ranch-style home offers 1,979 square feet of thoughtfully designed living space, combining timeless mid-century character with everyday comfort in one of Central Florida's most sought-after locations. Designed for effortless living, the home's spacious single-level floor plan provides nearly 2,000 square feet of functional space with no stairs to navigate. At the center of the home, inviting living and gathering areas are anchored by a charming built-in fireplace, creating a warm and welcoming atmosphere for relaxing evenings or entertaining family and friends. Year-round comfort is ensured with central electric air conditioning and a reliable forced-air heating system. At the same time, public water and sewer service through the City of Winter Park provide dependable, low-maintenance utilities. Best of all, there are no HOA fees or restrictions, giving you the freedom to enjoy your property without additional regulations or monthly dues. Situated on a generous 0.26-acre lot, the home offers ample outdoor space for gardening, recreation, or future enhancements. Its exceptional location places you just minutes from the renowned dining, shopping, parks, and cultural attractions of downtown Winter Park.

351 Starling Road, Winter Park

$650,000

2 Beds ⋅ 2 Baths ⋅ Mack Peter Rev SubDv. ⋅ 32789 Zip Code

Rare opportunity to own a charming Duplex on a corner lot in the heart of Winter Park! Located walking distance to Mead gardens and Orange Ave, and less than a mile from Park Ave. shopping and dining, this incredible investment is positioned for convenience and enjoyment! Across the street is a community garden. Whether you are looking for an investment property to add to your portfolio or a primary residence with income generating capabilities, this property has it all! New roof in 2024, and new windows and exterior paint in 2026. AC's updated in 2024 & 2025. Schedule a tour to secure this incredible investment today!

901 Harmon Avenue, Winter Park

$549,900

3 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge Add 02 SubDv. ⋅ 32789 Zip Code

Rare Waterfront Opportunity in Winter Park! Discover your own slice of Florida paradise with this waterfront gem offering 94 feet of direct canal frontage on Lake Bell for under $550,000!. Tucked away in a peaceful, private setting, yet just minutes from Winter Park’s famed Park Ave, Winter Park Village, College Park and Downtown Orlando with numerous shopping and dining options making this property the perfect blend of seclusion and convenience. Built in 1957, this classic Florida ranch features 3 bedrooms and 2 bathrooms within 1,837 SF of living space. Major updates include a new roof in 2024 and HVAC in 2019. Step inside off the covered front porch to find spacious living and dining areas highlighted by charming built-in features and abundant natural light. At the heart of the home, the kitchen offers easy access to a generous walk-in pantry/utility room/laundry area. The adjoining family room opens to a covered back porch overlooking the expansive backyard and tranquil canal. Situated on a .40-acre lot, the property extends beyond the canal, creating a natural wooded buffer that enhances privacy and provides a serene backdrop. Whether you envision a pool, outdoor kitchen, garden, or entertaining space, the backyard offers endless possibilities to create your dream outdoor oasis (subject to municipal review and approvals). Lake Bell is a 36-acre spring-fed ski lake with an average depth of 12 feet, ideal for boating, skiing, kayaking, paddle boarding and enjoying the Florida lifestyle. Fishing enthusiasts will also appreciate the lake’s reputation for largemouth bass and bluegill. Other notable exterior highlights include fenced in backyard, covered front entry, two rear porches and 1-car carport. The home is on septic that has been well maintained and serviced regularly.The location also offers quick access to Interstate 4 and close proximity to area hospitals, parks and cultural centers. Don’t miss this exceptional opportunity to own waterfront property in Winter Park/3789 at an incredible value!

1003 Lake Bell Drive, Winter Park

$235,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

NEW PRICE/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring throughout - tile and laminate for easy care...no carpet. Enjoy the dining space that opens to the large great room and balcony where you'll love sitting in the evenings to relax. SPACIOUS BEDROOMS - Primary bedroom has an attached full bathroom and bedroom 2 has a LARGE walk-in closet. The 2nd Full Bathroom is accessed via a common hallway. The Chateaux Du Luc LAKEFRONT COMMUNITY offers FABULOUS AMENITIES that include an oversized heated pool, clubhouse, community deck, BBQ grill, 2 on-site saunas, updated on-site laundry facilities, and a resident-only boat ramp on skiable Lake Killarney. There's even storage for your Kayak or paddleboard! Roof 2025. Reach out today for your personal showing!!

1500 Gay Road Unit 3C, Winter Park

300 Carolina Avenue Unit 402C, Winter Park

$650,000

3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

EXCEPTIONAL ELEGANCE & VALUE IN DOWNTOWN WINTER PARK now for JUST $650,000! This spacious 3-bedroom, 2-bath top-floor residence in the coveted PARK WEST community presents a rare opportunity to enjoy the best of Winter Park living just one block from Park Avenue. This residence offers an impressive combination of generous living space, architectural character, privacy, and an unbeatable location. Situated on the fourth floor, this distinctive condo features vaulted ceilings, skylights, and abundant natural light, creating an open and airy atmosphere throughout. Expanded living areas provide flexibility for entertaining, relaxing, or working from home. The inviting living room features a fireplace, while the spacious kitchen offers ample cabinetry, generous counter space, and a convenient breakfast bar. The thoughtfully designed floor plan includes three generously sized bedrooms, including a primary suite with vaulted ceilings, a walk-in closet, and a spacious bathroom. The second bedroom features a charming sunroom alcove and can connect to the primary suite, offering the flexibility of a private den, sitting room, or home office. Storage is exceptional, with a large IN-UNIT laundry room and an oversized attic — features rarely found in condominium living. Recent improvements include a NEW HVAC system, NEW water heater, and plumbing updates, providing added peace of mind. A reserved covered parking space and plentiful guest parking add everyday convenience. Beyond the residence, Park West offers a gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements. Association fees also include sewer and trash service, making this an appealing low-maintenance, lock-and-leave lifestyle! And the location is truly extraordinary! Enjoy the freedom to stroll to Park Avenue's acclaimed restaurants, boutiques, sidewalk cafés, museums, and year-round events, all just moments from your front door. With its spacious three-bedroom floor plan, top-floor privacy, and exceptional storage, this is an outstanding opportunity to enjoy downtown Winter Park living at a compelling value!

300 Carolina Avenue Unit 402C, Winter Park

$1,495,000

4 Beds ⋅ 2 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, ideal for today’s lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with durability and efficiency in mind. Major improvements include a commercial-grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home’s long-term value and performance. The outdoor spaces have been equally curated, with mid-century-inspired landscaping designed for beauty and ease of maintenance. Palms, agave and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances ambiance and function. Just moments from desirable Park Avenue, this architecturally significant modern residence is ideally in one of Winter Park’s sought-after neighborhoods, near Lake Virginia, Rollins College and Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north-facing orientation and beautiful natural light throughout the day.

446 Melrose Avenue, Winter Park

$524,900

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

In the sought-after Orwin Manor neighborhood, this beautifully updated one-story residence offers a seamless blend of comfort, style and convenience. Featuring three bedrooms and two baths, the home showcases an open-concept floor plan enhanced by engineered wood flooring that extends throughout every room, creating a cohesive and inviting living environment. The kitchen is thoughtfully updated with quartz countertops, refreshed cabinetry, newer appliances and a charming breakfast nook, ideal for casual dining. The living spaces flow effortlessly to a wonderful enclosed porch, providing additional year-round enjoyment, with direct access to an open brick-paver patio complete with a firepit, all set in a fully fenced backyard ideal for entertaining or relaxing in privacy. Both baths have been tastefully updated, and a new roof installed in 2021 that adds to the home’s overall appeal and peace of mind. Ideally just minutes from vibrant shopping and dining of downtown Winter Park and College Park, with convenient access to major roadways and the AdventHealth Orlando campus, this home offers exceptional accessibility to all metro Orlando has to offer. Whether as a primary residence or an investment opportunity, this property presents an exceptional offering in a prime, established location.

1741 Westchester Avenue, Winter Park

$1,595,000

3 Beds ⋅ 2 Baths ⋅ Tuscany Terrace SubDv. ⋅ 32789 Zip Code

Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue’s renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted “Vias” of Winter Park, a collection of streets long regarded as one of the city’s most established and desirable residential enclaves. The existing residence is perfectly livable and has benefited from numerous upgrades, offering flexibility for immediate occupancy while planning a future custom build. The home also presents excellent rental potential. Please note the interior is currently being utilized for storage and does not reflect its full presentation potential, providing an opportunity for cosmetic refresh or personalization. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end¦users alike — a rare chance to secure one of Winter Park’s most desirable land offerings in a highly established neighborhood.

1113 Via Del Mar, Winter Park

$849,000

2 Beds ⋅ 2 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.

560 Ololu Drive, Winter Park

$205,000

3 Beds ⋅ 2 Baths ⋅ Waterfall Cove At Winter Park SubDv. ⋅ 32789 Zip Code

This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.

1695 Lee Road Unit C202, Winter Park

Winter Park, Orlando, FL 2 Bathroom for Sale

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