Winter Park, FL Homes For Sale | Align Right Realty

Winter Park FL Real Estate & Homes for Sale

359 Properties Found

The median home value in Winter Park, FL is $526,250. This is higher than the county median home value of $318,000. The national median home value is $308,980. The average price of homes sold in Winter Park, FL is $526,250. Approximately 56% of Winter Park homes are owned, compared to 33% rented, while 11% are vacant. Winter Park real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Winter Park real estate agent to arrange a tour today!
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Beds:
3
Baths:
2.00
Sq.Ft.:
1,732
Status:
NEW LISTING
MLS#:
O6303962
Type:
Single Family
Subdivision:
WRENWOOD HEIGHTS
Lot size:
0.3 Acres
Year built:
1972
A broker reciprocity listing Courtesy: MARK SPAIN REAL ESTATE, 855-299-7653
View additional info

Charming Winter Park Home with PoolWelcome to 5001 Tangerine Avenue, a bright and welcoming 3-bedroom, 2-bath home in the heart of Winter Park. Situated on a spacious 0.32-acre lot, this 1,732 sq ft home features an inviting layout perfect for relaxing or entertaining.Enjoy sunny Florida days by your private pool and take advantage of the large yard for outdoor fun or future possibilities. Nestled in the peaceful Wrenwood Heights neighborhood, you're just minutes from Winter Park's parks, shops, and dining.Don't miss this comfortable and well-located home"your Winter Park retreat awaits!

Open House:

Saturday, 5/3 1:00-4:00PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
1,745
Status:
NEW LISTING
MLS#:
O6299729
Type:
Single Family
Subdivision:
CANTON AVE COTTAGES 1
Lot size:
0.12 Acres
Year built:
2017
A broker reciprocity listing Courtesy: COLDWELL BANKER RESIDENTIAL RE, 407-647-1211
View additional info

Rare find in the heart of Historic West Winter Park - Newer 2017 solid built David Weekley home now available! This modern designed chic home offers energy efficient features with luxury design. Walk into the home and be impressed by the voluminous ceilings and 8' door frames adorned with ceiling crown molding. This unique home design offers ultimate privacy with all bedrooms on the lower floor while the living/entertaining space is upstairs. Windows throughout the home filtrate a natural light that compliment the wooden floors. Upstairs you'll find the living space large and inviting. The chef's kitchen is spacious with abundant cabinetry and offers all stainless-steel Jenn Air appliances. The commercial style gas cooktop offers a wall mounted kettle water feature along with a flat surface griddle and is topped with a deco canopy range hood. The built-in bottom mount refrigerator is complimented alongside the programmable electric oven and convection/microwave. Center kitchen island doubles as dining space with room for four or there's room for a dining table. Solid wood cabinets are topped with glass doors to display stylish dinnerware. Dual pantry sliders with pull out drawers adjoin the wine refrigerator (Jenn Air of course) with additional cabinets. The Great Room's sliding glass doors welcomes you outside to the expansive maintenance free Hardee board deck. The deck is pre-plumbed for both water and gas to complete your grilling needs. The luxurious primary bedroom offers a tray ceiling and large walk-in closet. Venture into the impeccable primary bath and enjoy the huge walk in shower with built-in bench seat and overhead rain and wall mount shower heads. The additional two bedrooms share a bathroom accessible by each side but has a separate door to shower and toilet. The downstairs enormous laundry room is complete with a sink and additional cabinets. You'll find the garage oversized and can be described as 2.5 car size with epoxy coated flooring and an EV charger. Water Softner system stays - easy to use! There's an additional parking pad for your guests. The home is completely fenced and has energy efficient dual tankless gas water heaters and is prewired for 5.1 Surround sound audio. Best part of this small brick paved urban planned community - HOA pays for landscaping maintenance, plant replacement, mulch and sprinkler repair and you're connected to a natural gas utility service. Walk to the best shopping and dining available in Central Florida - Park Ave. and Winter Park Village. The Sunrail and Amtrak train depot is only 6 blocks away with Rollins College right around the corner. Easy commute to Downtown Orlando, Full Sail University and the Orlando International Airport. Best value in 32789 zip code!!! Call today for your showing.

Open House:

Sunday, 5/4 2:00-4:00PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
1,993
Status:
NEW LISTING
MLS#:
O6304121
Type:
Single Family
Subdivision:
MAITLAND SHORES FIRST ADD
Lot size:
0.23 Acres
Year built:
1953
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC, 407-645-4321
View additional info

Modern Midcentury Retreat with Luxe Upgrades & Private Community Lake AccessThis meticulously renovated 3-bed, 2.5-bath midcentury home blends timeless design with high-end contemporary finishes. Reimagined in 2021, it features an open floorplan highlighted by terrazzo flooring, quartz accent walls, and a cozy family room with bamboo floor and a gas fireplace.The sleek, chef-inspired kitchen showcases Italian Cento Per Cento wall tile, Thermador appliances including a 6-burner gas cooktop, double wall ovens (rotisserie + convection/steam), dual-zone wine fridge, Delorean-style cabinetry, and custom island lighting. A built-in pantry with pull-out shelving, cutlery storage, and a hydraulic lift mixer stand add both function and flair.Retreat to the Phil Kean-designed primary suite complete with king bed, nightstands, electric blinds, and integrated closet system. The ensuite spa bath features a Jacuzzi tub with high volume filler, separate high-pressure steam shower, Robern vanity, and inset medicine cabinet.Additional features include a 2-car garage with insulated door and interior storage, whole-house reverse osmosis water filtration, and a private backyard oasis with a saltwater pool and cabana.Enjoy exclusive canal access to Lake Maitland for small watercraft in this quiet, community.

Open House:

Saturday, 5/3 10:00-1:00PM

More Open House Info >

Beds:
3
Baths:
2.00
Sq.Ft.:
1,562
Status:
NEW LISTING
MLS#:
TB8379639
Type:
Single Family
Subdivision:
WINTER WOODS UNIT 03
Lot size:
0.21 Acres
Year built:
1970
A broker reciprocity listing Courtesy: LPT REALTY, LLC, 877-366-2213
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Seize this exceptional opportunity to acquire a remarkable property in the esteemed town of Winter Park. The roof is only four years old, with rain gutters around the entire house! The kitchen is update featuring a stone countertop, breakfast bar, and ample natural lighting. The GE refrigerator and stove top are 4yrs old. The professionally maintained oversized swimming pool adds to the property's allure. This home has been lovingly cared for and cherished by the same owner since 1972! Additional features include a new vinyl fence, new garage door, updated outdoor electrical box, lawn irrigation, and a wheelchair ramp in the garage. The asking price is a fair reflection of the property's current condition. Come and get your great deal, then make it your own inside and out.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,803
Status:
NEW LISTING
MLS#:
O6303931
Type:
Condo, Townhouse
Subdivision:
WINDWARD SQUARE SEC 1
Lot size:
0.09 Acres
Year built:
1978
A broker reciprocity listing Courtesy: WRA BUSINESS & REAL ESTATE, 407-512-1008
View additional info

Unmissable opportunity in Winter Park! Beautiful house for sale with 3 bedrooms and 3 bathrooms, perfect for those seeking comfort, convenience and quality of life.Located in one of the most sought-after areas of Winter Park, with an excellent location, close to schools, shops, restaurants, parks and much more!The community offers a complete infrastructure with a swimming pool, playground, sidewalks for walking and a family environment ideal for all ages.Don't miss this chance to live well!Schedule your visit and come see your new home!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,618
Status:
NEW LISTING
MLS#:
O6303755
Type:
Single Family
Subdivision:
PARKLANDO
Lot size:
0.17 Acres
Year built:
1938
A broker reciprocity listing Courtesy: CORCORAN PREMIER REALTY, 407-965-1155
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Welcome to this delightful 1,600 sqft home in one of Winter Park's most coveted neighborhoods. This three-bedroom, two-bathroom home blends classic charm with modern updates. The beautifully updated kitchen features newer appliances and opens to a cozy living area with a character-rich wood-burning fireplace. The versatile 23'x11' living and dining area offers multiple configuration options, perfect for entertaining or creating dedicated spaces for different activities. A welcoming brick paver courtyard with charming arbor overhead creates a picturesque entrance. French doors open to a covered patio, perfect for outdoor living. Situated in a well-established neighborhood with new custom-built homes, this property balances mature community charm with contemporary design influences. The location is unbeatable - within easy walking distance to highly-rated Audubon Park K-8 school, the thriving Audubon Park Garden District restaurants, and unique boutique shopping. Just minutes away, you'll find Baldwin Park Village Center with it's Michelin Star rated restaurants, the vibrant Mills/50 District, and the iconic Park Avenue experience. This exceptional home offers the quintessential Winter Park lifestyle in a location that combines established neighborhood character with exciting urban accessibility.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,248
Status:
NEW LISTING
MLS#:
O6303604
Type:
Single Family
Subdivision:
ACREAGE
Lot size:
0.41 Acres
Year built:
2015
A broker reciprocity listing Courtesy: OLDE TOWN BROKERS INC
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Get Busy Living the Winter Park lifestyle in this custom 4-bedroom, 4.5-bathroom pool home tucked away at the end of a 150-foot private drive with gate. Designed with comfortable yet sophisticated living space, this home is perfect for those seeking a serene retreat for both everyday living and entertainment. The heart of the home is the sizable kitchen, boasting a gas stove, high-end appliances, and a truly unique island crafted from reclaimed wood with a solid concrete countertop " a perfect blend of rustic charm and modern design. The primary retreat is conveniently located on the first floor, featuring a spa-like bathroom complete with a soaking tub and a spacious walk-in shower. Upstairs, you'll find two additional ensuite bedrooms with the 4th bedroom that doubles as a home office complete with built-in desk and murphy bed. A generously sized bonus room/living area upstairs provides additional flexibility for a media room, playroom, or home office. Outdoors, the professionally designed and illuminated landscaping sets a warm, welcoming tone which includes a spectacular 12' x 40' salt-filtered heated pool surrounded by a luxurious travertine deck with fire-pit. Close proximity to all the charm and amenities Winter Park has to offer. This exceptional home offers privacy, elegance, and thoughtful design at every turn. Call today for an easy showing!

Beds:
5
Baths:
4.00
Sq.Ft.:
3,068
Status:
NEW LISTING
MLS#:
O6303680
Type:
Single Family, Ranch
Subdivision:
TIMBERLANE
Lot size:
0.27 Acres
Year built:
1956
A broker reciprocity listing Courtesy: LPT REALTY, LLC, 877-366-2213
View additional info

This home is the perfect blend of resort luxury and farmhouse charm, with high-end finishes and features that cater to both relaxation and entertaining. From the resort-style backyard with a magnificent Saltwater Pool, lovely green space around the koi pond to the HGTV-worthy Interior with an entertainer's dream kitchen, this has it all. The spacious split-bedroom floor plan, luxurious primary suite, and thoughtfully designed storage make it both stunning and practical. The large lanai with fireplace and full wet bar, beautifully landscaped fenced in yard, pond, green space and even storage for your boat, outdoor toys or dog run"every detail seems meticulously planned to maximize comfort and style. It's clear that this home was built for the love of hosting, relaxing, and living life to the fullest. 5 Bedroom, 4 Bath, Pool Home with 2-Car Garage (NEW Genie Garage Door Opener). Long pavered driveway with plenty of room for all of your vehicles. You can't help fall in love with this Fully Renovated Florida Ranch Home. Walk into the impeccable warm and welcoming split Bedroom floor plan that offers a spacious Primary Bedroom in the rear of the home with beautifully updated Primary Bath. Double Vanity, Granite countertop, Chocolate Brown Cabinets, Tiled Walk-in Shower with Frameless Glass Doors. Two closets in Primary, one walk-in and one reach-in closet. Both front bedrooms are En-Suites. Bedrooms 4 and 5 share hall bathroom with tub and shower. If you are a chef or just a foodie you won't want to leave this Ultimate Gourmet Kitchen. Zline 6-Burner, Griddle, Professional grade gas range with double electric oven and Zline wall mounted range hood. Dishwasher, two stainless steel farm sinks, wall-mount pot filler, microwave oven and French Door Refrigerator. White Shaker Soft Close, Kitchen Cabinets with Black hardware and high-end granite countertops, adorned by Designer Stone Backsplash. Behind the custom-built barn doors is the laundry closet and pantry. The large 7.9 x 5.3 Island seats 6 comfortably. This Dining Room is meant for entertaining. Seats 10-12 comfortably with sideboard, bar hutch and more. Open the French doors and instantly double your hosting space. Living Room is warm and cozy with wood burning fireplace, built-ins, LED recessed lighting. Flooring throughout is porcelain wood-look tile. Looking for a home with storage, this home has custom built-in cabinets in 2 bedrooms and hallway. You'll be amazed how much you can store. If you enjoy outdoor living and entertaining, you'll never want to leave home. Step outside to a spacious covered lanai with tongue and groove ceiling, wood plank flooring, fireplace, TV and surround sound speakers. Full wet bar, lower stone encased with granite tops. Porch Swing. Fence has double gate on left side of home so you can easily pull your boat, RV or extend this into more garage area. Enjoy the mature Florida landscape as you sit by the pool and bar enjoying your favorite team on the TV with your friends. Pool remarcited and tiled in 2022. New pool equipment 2023, Pool Shed is to the right of the house behind the bar to hold all of your pool supplies. New HVAC 2023. Compressor 2020. Roof was replaced in 2018, house was replumbed and rewired in 2020. All Double Pane Aluminum Windows throughout home.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,804
Status:
NEW LISTING
MLS#:
O6304495
Type:
Single Family
Subdivision:
GALLOWAY PLACE REP
Lot size:
0.19 Acres
Year built:
1948
A broker reciprocity listing Courtesy: FLORIDA HOMES REALTY & MTG, 904-996-9115
View additional info

Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is full of timeless charm and unlimited potential! Set on a private lot in the heart of Winter Park, moments from Rollins College, Park Avenue, and Winter Park Hospital. Just a short walk provides coveted access to the Winter Park Chain of Lakes, bring your paddle board or canoe. Step inside the spacious formal living room with a gas fireplace and original hardwood floors. The updated kitchen with Carrara quartz countertops, quality wood cabinetry, a large pantry and ample storage opens to the dining and sunrooms. A wall of French and glass doors in the sunroom"spanning the length of the home"creates a seamless indoor-outdoor connection to the covered patio and beautifully landscaped garden. Paver walkways through lush greenery, guide you to a tranquil cabana, a serene retreat perfect for both relaxation and hosting guests. The primary suite is a peaceful retreat offering direct access to both the interior and exterior through elegant French doors. It features an updated ensuite bath and a spacious cedar-lined walk-in closet, combining luxury with thoughtful functionality. A spacious and functional split floor plan ensures privacy, with two generously sized guest bedrooms located on the opposite side of the home. Each room showcases rich hardwood floors, plantation shutters, and walk-in closets. A beautifully renovated guest bath adds style and comfort, making it ideal for family or visitors. The attached single car garage with washer, dryer and a circular drive offers ample parking and easy access. The freshly painted interior (2025) is a blank canvas for your vision! This home is a perfect blend of classic charm and modern updates. Schedule your showing today!

Open House:

Saturday, 5/3 1:00-3:00PM

More Open House Info >

Beds:
2
Baths:
2.00
Sq.Ft.:
913
Status:
NEW LISTING
MLS#:
O6302829
Type:
Condo, Townhouse
Subdivision:
MEAD GARDEN
Lot size:
0.02 Acres
Year built:
1967
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES, 407-644-1234
View additional info

Welcome to this beautifully maintained 2-bedroom, 2-bath condo in the serene community of Mead Gardens. This second-floor unit offers the ease of single-level living once inside, featuring an open-concept layout filled with natural light. The updated kitchen (2016) boasts stylish tile flooring that mimics hardwood, granite countertops, a farmhouse sink, and stainless-steel appliances, all overlooking the spacious great room. One of the property's standout features is the spacious private balcony overlooking the lush beauty Mead Gardens. The balcony offers privacy and tranquility as there are no rear neighbors. The primary suite offers a peaceful garden view, an ensuite bath with walk-in shower and a single vanity. The second bedroom features sliding doors to the front entry and has easy access to a full guest bathroom with a tub/shower combo. Residents enjoy access to a sparkling community pool, laundry facilities, and mailboxes just steps away. Enjoy this prime Winter Park location, located just minutes from Park Avenue and Rollins College.

Open House:

Saturday, 5/3 11:00-1:00PM

More Open House Info >

Beds:
3
Baths:
4.00
Sq.Ft.:
3,112
Status:
NEW LISTING
MLS#:
O6302823
Type:
Condo, Townhouse
Subdivision:
WINTER PARK RESIDENTIAL
Year built:
2008
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC, 407-645-4321
View additional info

Discover luxury living in this exquisite two-story condominium, located on the third floor of the highly sought-after Douglas Grand. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends entertaining with everyday comfort. Step into a blank canvas offering a clean landscape"free of flooring"allowing you to effortlessly bring your own design vision to life. Whether you envision warm hardwood, sleek tile, or cozy carpet, this space is designer-ready and primed for your perfect finish. Be immediately impressed by the inviting open floor plan filled with natural light, high ceilings, and detailed crown molding. The gourmet kitchen is a chef's dream, featuring a spacious breakfast bar island, custom wood cabinetry, granite countertops, and a built-in desk. Enjoy casual dining in the heart of the home with a charming breakfast nook, perfectly positioned for morning coffee or quick weeknight meals. Step through elegant French doors into your own private, enclosed atrium"a versatile outdoor retreat ideal for alfresco dining, quiet relaxation, or entertaining guests in style. The main level features a seamless living and dining area, along with a private downstairs bedroom with en suite bath and walkout balcony"ideal for guests, in-laws, or a home office. Upstairs, the primary suite is a serene sanctuary with an indulgent soaking tub, dual granite-topped vanities, and an expansive walk-in closet. French doors lead to a large private balcony offering sweeping views of Winter Park's iconic Park Avenue"the perfect backdrop for morning coffee or evening unwinding. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. The convenience of an upstairs laundry room enhances daily living, while a spacious storage closet offers the potential for an elevator, adding long-term accessibility and value. Enjoy peace of mind with a secure, gated garage offering two reserved parking spaces. Situated in the heart of Winter Park, the Douglas Grand places you steps away from Park Avenue, the Farmers' Market, Rollins College, Hannibal Square, the Winter Park Golf Course, WP Tennis Center, Winter Park Village, and more. Embrace the effortless downtown lifestyle at the Douglas Grand! A few notable upgrades include brand new front elevation windows and French doors (2024), interior paint (2024), and AC (2022).

Open House:

Sunday, 5/4 12:00-2:00PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
1,727
Status:
NEW LISTING
MLS#:
O6296942
Type:
Condo, Townhouse
Subdivision:
MERRIE OAKS VILLAGE PH 01
Lot size:
0.07 Acres
Year built:
1973
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES, 407-644-1234
View additional info

Welcome to 264 Balfour Drive " an exclusive residence within a private enclave of just 13 elegant townhomes in the heart of Winter Park designed by architect Nils Schweizer. a student of Frank Lloyd Wright. Offering an attached two-car garage and a premier location, this home blends sophistication with comfort in every detail.Step into a grand living room where soaring ceilings and expansive windows bathe the space in natural light. The formal dining room transitions effortlessly into a thoughtfully designed galley kitchen, showcasing a newly renovated island, high-end Bosch dishwasher, and a French door leading to a truly remarkable outdoor retreat.The covered courtyard, adorned with a trellised garden and overlooking manicured community green space, offers the perfect setting for elevated entertaining and tranquil evenings under the stars.Upstairs, discover a versatile loft ideal for a refined home office, along with a luxurious primary suite featuring a glass-enclosed porch " a serene escape for morning coffee or evening unwinding. Two additional guest bedrooms and a well-appointed guest bath complete the upper level.This discreet and desirable community offers unmatched access to shopping, dining, Advent Health Medical Campus, Full Sail University, Cady Way Park with bike trails & pickleball courts and a short drive to the renowned charm of Park Avenue. Roof 2012, HVAC 2016. Zoned for top-rated schools: Brookshire Elementary, Glenridge Middle, and Winter Park High. WELCOME HOME!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,192
Status:
NEW LISTING
MLS#:
O6303093
Type:
Single Family
Subdivision:
PRESERVE AT HAWKS CREST
Lot size:
0.14 Acres
Year built:
2019
A broker reciprocity listing Courtesy: SELECTA REALTY LLC, 407-777-7131
View additional info

Welcome to your future home, where style, comfort, and technology come together seamlessly. This stunning 4-bedroom, 3-bath residence is nestled in the highly desirable gated community of Hawks Crest, known for its luxurious resort-style amenities and unbeatable location.From the moment you enter, you'll be greeted by a spacious and thoughtfully designed open-concept layout, perfect for both everyday living and entertaining. Custom trim details and accent walls adds a touch of sophistication to the living and dinning roomThe gourmet kitchen is truly the heart of the home, showcasing elegant quartz countertops, beautiful cabinets, stainless steel appliances, double ovens, and ambient recessed lighting that enhances the inviting feel of the living space.Retreat to the expansive primary suite, with a walk-in shower with decorative tile, and a generously sized walk-in closet. Ideal for hosting guests, the split floorplan includes a private guest suite with its own full bathroom. Two additional comfortable bedrooms, ample closet space, and flexibility for a home office, nursery, or hobby room.Enjoy the added convenience of an indoor laundry room with a utility sink, as well as a spacious two-car garage. Step outside to an extended paver patio"perfect for outdoor dining, entertaining, or simply enjoying the Florida sunshine. And to top it all off, this home features a private backyard oasis, complete with a sparkling pool and tranquil waterfall feature, all beautifully surrounded by elegant pavers and offering a peaceful water view of a nearby pond"the perfect setting for relaxation or entertaining in true Florida style.This home is equipped with a comprehensive smart home system that controls everything from the front door and thermostat to the ovens, irrigation, and security features like the Ring doorbell"all at your fingertips. Energy efficiency is top of mind with spray foam insulation and energy-efficient windows, helping you stay comfortable while keeping costs down.Hawks Crest offers peace of mind with a gated entrance and virtual guard, and its resort-style community center includes a sparkling pool with sun shelf and cabanas, fitness center, clubhouse, grilling stations, playgrounds, a dog park, and private access to Lake Howell, complete with a fishing pier and kayak launch.Ideally located, you're just minutes from charming Downtown Winter Park, with its boutique shopping and dining scene, and within easy reach of Rollins College, UCF, top-rated hospitals, beaches, and Orlando's world-famous attractions like Walt Disney World and Universal Studios.This home is the perfect blend of elegance, convenience, and modern functionality. Don't miss this opportunity"schedule your private showing today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,085
Status:
NEW LISTING
MLS#:
O6303221
Type:
Condo, Townhouse
Subdivision:
WINTER PARK WOODS CONDO
Lot size:
0.2 Acres
Year built:
1974
A broker reciprocity listing Courtesy: JADE KEY REALTY LLC
View additional info

Welcome to 316 Scottsdale Square, a delightful 2-bedroom, 1 and half bathroom condo located in desirable Winter Park. This home features a spacious open floor plan with natural light, ideal for comfortable living. The kitchen includes modern appliances and overlooks the cozy living area, perfect for entertaining. The utility room is equipped with a washer and dryer, plus extra storage space for added convenience. The master bedroom features a walk-in closet, and the second bedroom is perfect for guests or a home office. Located in a quiet, well-maintained community, this condo offers easy access to nearby shopping, dining, and entertainment options. This condo has everything you need for comfortable living in Winter Park! Don't miss this opportunity to make this your new home.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,250
Status:
NEW LISTING
MLS#:
S5125620
Type:
Condo, Townhouse
Subdivision:
WINTER PARK WOODS CONDO
Lot size:
0.2 Acres
Year built:
1974
A broker reciprocity listing Courtesy: VYLLA HOME, 407-377-5900
View additional info

Short Sale. Short Sale. Short Sale. SHORT SALE. SHORT SALE, AS IS,Location, Location, Location Winter Park, Excellent opportunity to own a townhome 3/2, close to everything. to express way and restaurants

Beds:
3
Baths:
3.00
Sq.Ft.:
2,145
Status:
NEW LISTING
MLS#:
O6302902
Type:
Single Family, Ranch
Subdivision:
FLORA PARK FIRST ADD
Lot size:
0.36 Acres
Year built:
1974
A broker reciprocity listing Courtesy: COLDWELL BANKER RESIDENTIAL RE, 407-647-1211
View additional info

Charming, Well-Maintained Home on a Prime Lot in Winter Park's Coveted Tree StreetsDon't miss this rare opportunity to own a beautifully landscaped and meticulously maintained property on one of the most desirable streets in Winter Park. Situated on one of the largest lots in the sought-after Tree Streets, this home is perfect for a buyer or builder ready to create something truly special in an exceptional neighborhood.Approved by the City Planner for expansion up to 5,500 sq ft, this property offers immediate move-in readiness with future potential. Recent updates include a newer roof (2021), HVAC system (2020), updated flooring, fresh paint, and modern appliances throughout.As you enter, your eyes are immediately drawn to the stunning screened-in pool area"ideal for entertaining or relaxing under the impressive 47' x 14' covered lanai. The pool has been recently resurfaced with PebbleTec for low-maintenance luxury.Inside, the home features a thoughtfully designed layout with three bedrooms, including a private primary suite, separate from the main living areas for quiet retreat. Enjoy two spacious living rooms, a formal dining room, dedicated office space, and a large kitchen that offers endless possibilities for customization.Zoned for top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High. Just minutes from the boutiques and dining of Park Avenue.This is more than a home"it's an opportunity to live in one of Winter Park's most iconic neighborhoods.

Beds:
5
Baths:
5.00
Sq.Ft.:
3,983
Status:
NEW LISTING
MLS#:
O6301897
Type:
Single Family
Subdivision:
CYPRESS RESERVE
Lot size:
0.24 Acres
Year built:
1999
A broker reciprocity listing Courtesy: COMPASS FLORIDA LLC
View additional info

Welcome to 2832 Bear Island Pointe in Winter Park's premier gated community, Cypress Reserve! This meticulously maintained estate-like home is move-in-ready with 5 bedrooms plus a large office room with its own bathroom and separate exterior entry. Nestled near the serene Bear Gully Lake, this stunning residence offers the perfect blend of elegance, convenience, and resort-style living. The thoughtfully designed floor plan features a spacious first-floor primary suite with a spa-like ensuite, including double vanities, a soaking tub, a walk-in shower, and a generous walk-in closet (11x13 ft). A gourmet kitchen with granite counter tops and stainless steel appliances makes meal preparation effortless, while the formal living and dining rooms provide an ideal setting for entertaining. With five versatile bedrooms, there is plenty of space for guest rooms, home offices, a gym, or a library. High ceilings (11 feet) throughout the home enhance the open and airy feel. The laundry room is equipped with a stackable washer and dryer, built-in cabinets, and a sink for added convenience. The outdoor space is an entertainer's dream, featuring a large screened-in pavered patio, an indoor pool and spa, and a built-in barbecue area perfect for hosting gatherings. A spiral staircase leads to a private balcony off the primary suite, offering a peaceful retreat with beautiful views. This home is also equipped with solar panels (owner owned), providing an energy-efficient solution that helps reduce utility costs while promoting sustainable living. Perfectly positioned between world-famous beaches and major attractions, this home is just minutes from top-rated schools, including UCF, Rollins College, Trinity Prep, and The Master's Academy. It also offers easy access to Orlando International Airport, premier healthcare facilities, and the scenic Seminole Trail. Experience the best of Winter Park living in this exceptional home. Schedule your private showing today.

Open House:

Sunday, 5/4 1:00-3:00PM

More Open House Info >

Beds:
3
Baths:
4.00
Sq.Ft.:
3,096
Status:
NEW LISTING
MLS#:
O6301846
Type:
Single Family, Ranch
Subdivision:
PARK NORTH
Lot size:
0.38 Acres
Year built:
1968
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES, 407-644-1234
View additional info

Endless Potential in the Heart of Park North!Just steps from the charm and energy of Winter Park's Park Avenue"where boutique cafs, fine dining, art galleries, museums, Central Park, and the Winter Park 9 Golf Course await"this rare Park North gem offers the ultimate opportunity to create your dream home.Nestled at the end of a peaceful cul-de-sac, this expansive .38-acre lot (16,534 SF) is a true find in one of Winter Park's most desirable neighborhoods. Whether you're looking to build new or renovate the existing residence, the possibilities here are limitless.The current single-story block home spans nearly 3,100 square feet, with strong bones and a layout designed for easy living. Inside you'll find oversized rooms, a cozy fireplace, a spacious eat-in kitchen, an indoor laundry room, private office off the primary suite, and a 2-car garage. Recent updates"new roof (2023), updated electrical panel (2023), one A/C (2019) and modernized windows and doors"set the stage for your vision to come to life.Natural light fills the home, and the beautifully landscaped backyard offers a serene retreat with a private patio, rear privacy wall, and metal fencing"ideal for both everyday relaxation and stylish entertaining.Located in the coveted Winter Park school district, this is a rare chance to invest in a premium property with endless upside. Whether you choose to reimagine the existing home or build brand new, this is a canvas just waiting for your personal touch.Schedule your private showing today and explore the possibilities!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,729
Status:
NEW LISTING
MLS#:
O6302854
Type:
Single Family
Subdivision:
NORTHWOOD TERRACE
Lot size:
0.19 Acres
Year built:
1953
A broker reciprocity listing Courtesy: ORLANDO HOMES GROUP LLC, 407-923-6524
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Prime Development Opportunity in Winter Park near Audubon Park. Lot Size - 79' x 103' - 8212 sq. ft. Zoning - R-1A. FAR - 3530. Seize this exceptional opportunity to develop in the heart of one of Winter Park's most coveted neighborhoods. This 8,212 sq ft lot is ideal for a new construction project or a comprehensive renovation. Surrounded by new and renovated homes, this area is experiencing rapid appreciation. Zoned for Audubon Park K-8 and Winter Park High School, both highly regarded institutions. Enjoy walking distance to local favorites like East End Market, Kelly's Ice Cream, Redlight Redlight, and Sushi Lola.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,360
Status:
NEW LISTING
MLS#:
O6297693
Type:
Single Family, Ranch
Subdivision:
KENILWORTH SHORES SEC 04
Lot size:
0.26 Acres
Year built:
1962
A broker reciprocity listing Courtesy: KELLER WILLIAMS WINTER PARK, 407-545-6430
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Welcome to one of the most sought after neighborhoods of Kenilworth Shores in Winter Park! Nestled among tree-lined streets where the mail is still delivered right to your door, this beautifully appointed 4-bedroom, 3-bathroom home blends timeless elegance with modern comfort. From the moment you step onto the charming brick walkway, you'll fall in love with the lush, mature landscaping and inviting curb appeal. Enter through stately double doors into a home filled with thoughtful details"gleaming hardwood floors, crown molding, chair rail, and classic columns in the living, dining, and family rooms. The functional and spacious kitchen is ready for gatherings large or small, whether it's a festive Thanksgiving dinner or a casual poolside barbecue. A flexible space off the kitchen serves as the perfect spot for a breakfast nook, mudroom, or home office. The primary suite, seamlessly added in 2013, offers a private retreat with its own office/flex space, custom walk-in closet, and French doors opening to the pool area. The luxurious en-suite bath features a pedestal soaking tub, dual vanities, and a large walk-in shower with dual shower heads. Three additional bedrooms are situated on the opposite side of the home, including a secondary primary bedroom with its own en-suite bath"perfect for guests or multigenerational living. Step outside to your private tropical paradise featuring a spacious screened lanai, sparkling pool with sun shelf, fountains, and spa jets"an entertainer's dream. Located just minutes from the Cady Way Pool, tennis and pickleball courts, playgrounds, Ward Park, Center for Health and Wellbeing, WP AdventHealth Hospital & ER, and top-rated schools (Brookshire, Glenridge and Winter Park High School) and colleges like Rollins, Full Sail, Valencia, and UCF. Plus, you'll love the convenience of nearby shops, restaurants, and grocery stores. Less than 10 minutes from Downtown Winter Park shopping and fine dining. This is more than a home"it's a lifestyle. Come experience it for yourself!ROOF - 2013 HVAC - 2013 ELECTRICAL UPDATES - 2013 PLUMBING - 2022 WATER HEATER - 2022

Open House:

Sunday, 5/4 1:00-4:00PM

More Open House Info >

Beds:
4
Baths:
4.00
Sq.Ft.:
3,377
Status:
NEW LISTING
MLS#:
O6301703
Type:
Single Family, Ranch
Subdivision:
DOMMERICH COVE
Lot size:
0.37 Acres
Year built:
1964
A broker reciprocity listing Courtesy: KELLER WILLIAMS ADVANTAGE III, 407-207-0825
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A RARE Winter Park Estate Blending TIMELESS CRAFTSMANSHIP with MODERN FLEXIBILITY & RESORT-STYLE Living comes to market for the FIRST TIME. 2923 Cove Trail is nestled between the best of Winter Park & Maitland. Masterly created by the renowned Charlie Clayton it blends unmatched craftsmanship with modern design & flexibility craved by you, today's discerning buyer. REIMAGINED in 2011 this 4-bedroom, 4-bath home features WHITE OAK FLOORS, SOLID WOOD CABINETS, CARRERA MARBLE & TRAVERTINE finishes, along side preserved architectural details like SKIP TROWEL CEILINGS & CROWN MOLDING. Updates fashioned TWO PRIMARY SUITES offering ultimate privacy & flexibility.These SPLIT PLAN suites pack personality. The first provides a POOL VIEW, large WALK-IN CLOSET & SHOWER, while the second basks in the PRIVACY of its own SCREENED GARDEN PATIO & access to a COZY FLEX ROOM with BUILT-INS. Whether used as a SERENITY ROOM, craft space, or restyled into a KITCHENETTE this space adds rare flexibility. Flexibility & MULTIGENERATIONAL living in a ONE STORY home aren't the only rarities you'll marvel over. A LARGE SEPARATE OFFICE with PRIVATE EXTERIOR ENTRANCE provides an ideal location for professionals to consult with clients or social media influencers & podcasters to ply their trades. Imagine the freedom & peace of mind you'll gain not having to worry about traffic while also freeing your business from overhead & lease costs. When the workday ends, entertaining begins & other shiny facets of this home sparkle. A 2,500-BOTTLE CLIMATE-CONTROLLED WINE CELLAR sets the stage for unforgettable gatherings. Whether selecting a vintage for a romantic dinner, indulging guests with formal tastings or kicking back for a relaxed evening you're sure to savor these moments especially when you move the party outdoors to your PAVERED PATIO adjoining the cool blue waters of your 18x36 RESORT-STYLE POOL all tucked within the PRIVACY of lush 8-foot WALLS. Don't forget the patio is plumbed for an OUTDOOR BBQ & the pool for SOLAR HEAT when you're ready to add them.The outdoors isn't the only place you & your guests will gravitate to. Indoors, enjoy seamless FLOW between the SUNROOM, LIVING room, & FAMILY rooms. BUILT-IN SPEAKERS & STEREO SYSTEMS effortlessly deliver music to your ears. FIREPLACES in both living areas add warmth & ambiance for every season. Some properties claim to have a CHEF'S KITCHEN. This one delivers. Beyond the aesthetic updates, your cooking talents will flourish as you pivot between the island PREP SINK, professional grade 6-BURNER GAS COOKTOP with POT FILLER exceptional overhead VENT, BUILT IN OVENS & stainless steel FRENCH DOOR REFRIGERATOR. For those extra busy celebrations, just around the corner in the laundry room a complement of CABINETS,2ND FULL FREEZER & 2nd REFRIGERATOR await your handiwork while the WASHER & DRYER stand ready for tidying. There's so much more, but here are a few more highlights:IMPACT-RESISTANT WINDOWS, a PARTIAL HOME GENERATOR, IRRIGATION ON WELL, owned SECURITY SYSTEM & 3 BUILT-IN SAFES" all contributing to your long-term comfort & the home's efficiency. There's NO DOUBT this property DELIVERS UNMATCHED VALUE, & QUALITY in one of Winter Park's MOST DESIRABLE neighborhoods. Homes of this CALIBER RARELY COME TO MARKET" AND WHEN THEY DO THEY DON'T LAST. SCHEDULE your private showing TODAY. This is more than a home " IT'S the LIFESTYLE UPGRADE You've been WAITING FOR. *CLICK on Virtual tour link for 3D Walk Through.*

Beds:
4
Baths:
4.00
Sq.Ft.:
3,005
Status:
Active
MLS#:
O6302366
Type:
Single Family
Subdivision:
LAKEVIEW TERRACE
Lot size:
0.19 Acres
Year built:
2026
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY, 407-644-3295
View additional info

Pre-Construction. To be built. Welcome to a stunning new construction residence that redefines modern luxury and comfort. Located in a highly sought-after neighborhood, this thoughtfully designed 4-bedroom, 4-bathroom home spans 3,005 square feet and offers a seamless blend of elegance, functionality, and contemporary style. Built by Valdara Custom Homes"renowned for their exceptional craftsmanship and commitment to quality"This home showcases meticulous attention to detail and premium-quality finishes throughout. From the moment you enter, you are greeted by expansive open living spaces that invite natural light and create an atmosphere of warmth and sophistication.The open-concept floor plan is ideal for both everyday living and entertaining, featuring soaring ceilings, oversized windows, and a fluid layout connecting the gourmet kitchen, dining area, and spacious great room. Each bedroom offers a private retreat with generous closet space and spa-like bathrooms, including a luxurious primary suite designed for ultimate relaxation. High-end appointments such as designer fixtures, top-tier appliances, and custom cabinetry complement the home's modern aesthetic. Whether you're enjoying a quiet evening with family or hosting a lively gathering, this home provides the perfect backdrop for every occasion.Situated in a vibrant community with access to excellent schools, shopping, dining, and recreational amenities, this property offers a balanced lifestyle with both tranquility and convenience at your doorstep. Discover the unmatched quality and comfort of new construction living in a home designed to elevate your everyday experience.

Open House:

Sunday, 5/4 1:00-5:00PM

More Open House Info >

Beds:
3
Baths:
2.00
Sq.Ft.:
1,844
Status:
Active
MLS#:
O6302569
Type:
Single Family
Subdivision:
WINTER PARK PINES
Lot size:
0.21 Acres
Year built:
1963
A broker reciprocity listing Courtesy: EXP REALTY LLC, 407-476-4127
View additional info

One or more photo(s) has been virtually staged. Fully Renovated - EXPERIENCE WINTER PARK! This beautifully updated quarter acre Medallion Home offers 3 spacious bedrooms and 2 full bathrooms, with a bright open-concept layout and an inviting Florida room that overlooks a private, tree-lined backyard"perfect for family gatherings, peaceful mornings, or relaxed evenings at home.Your home gives you the opportunity to have access to an A-rated school district in a highly sought-after Winter Park community"a community that delivers the feel of an upscale HOA, WITHOUT THE FEES. Here, you can enjoy the convenience of one of the area's premier 18-hole golf courses, a 2.5-mile scenic nature trail ideal for biking or morning jogs, a 66-Acre expansive park full of mature trees and open green space for you and your family. More activities mean more fun outside of home! You also have access to an Olympic-sized community pool, beach volleyball, tennis and pickleball courts, as well as fields for soccer, baseball, and football"all of these just a short walk or bike ride away, and most importantly, available to you at NO additional cost.This is your opportunity to live in a thoughtfully renovated home in a community that offers both serenity and vibrant activity, right outside your doorstep.

Beds:
2
Baths:
1.00
Sq.Ft.:
954
Status:
Active
MLS#:
O6302210
Type:
Single Family
Subdivision:
GOLFVIEW
Lot size:
0.21 Acres
Year built:
1945
A broker reciprocity listing Courtesy: EMPIRE NETWORK REALTY, 407-440-3798
View additional info

BUILD YOUR DREAM HOME IN WINTER PARK!Nestled directly across from the historic Dubsdread Golf Course, this property offers a unique chance to invest in one of Orlando's most sought-after neighborhoods. Situated on a generous 150' x 60' lot along Midiron Drive"a street experiencing a transformation with homes reaching over a million-dollar mark"making this property perfect for redevelopment.Living here places you at the heart of Orlando's vibrant lifestyle. Enjoy close proximity to Winter Park Village, Advent Health, UCF Downtown Campus, and the Dr. Phillips Center for the Performing Arts. A plethora of shopping and dining options are just minutes away. Schedule your showing and don't miss this incredible opportunity!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,887
Status:
Active
MLS#:
TB8376138
Type:
Single Family
Subdivision:
MAITLAND SHORES FIRST ADD
Lot size:
0.19 Acres
Year built:
1953
A broker reciprocity listing Courtesy: FLAT FEE MLS REALTY, 813-642-6030
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?913 Moss Ln, Winter Park, FL 32789 is a beautifully renovated 3-bedroom, 2-bathroom single-family home that seamlessly blends mid-century charm with modern updates. Situated in the desirable Maitland Shores neighborhood, this split-level residence offers 1,887 square feet of comfortable living space on a 70 x 120 lot.Key Features:Recent Renovations: In 2023, the home underwent significant updates, including contemporary finishes, new flooring, fresh interior and exterior paint, and modern lighting throughout. Living Spaces: The main floor features a formal living room with a wood-burning fireplace, a formal dining room, a fully updated kitchen, and a Florida room. Upstairs, you'll find three generously sized bedrooms and two full bathrooms.Kitchen: The modern kitchen boasts quartz countertops, stainless steel appliances, a stylish backsplash, and ample cabinetry for storage"perfect for the home chef. Outdoor Living: The backyard is a peaceful oasis, featuring lush landscaping and a freshly updated patio space ideal for entertaining or relaxing under the Florida sun. Additional Amenities: The property includes a 2-car attached garage, mature landscaping, and a shed for extra storage. Location Highlights:Water Access: Residents enjoy limited access to the Winter Park Chain of Lakes, with a neighborhood entry point just one block away. Community: The home is located on a quiet, tree-lined street and is within walking distance to the Winter Park Racquet Club. It's also just minutes from downtown Winter Park, offering boutique shopping and fine dining along Park Avenue. Schools: Zoned for top-rated schools, including Dommerich Elementary, Maitland Middle, and Winter Park High School.

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