Cooper & Sewell Addition Homes for Sale

5 Beds ⋅ 4 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code

Welcome to The Birdhouse, one of Downtown Winter Garden's most iconic residences. Situated just blocks from Plant Street, the West Orange Trail, and the shores of Lake Apopka, this remarkable property offers a rare opportunity to own a thoughtfully restored home that seamlessly blends timeless architecture with modern luxury. Set on an expansive and highly coveted 0.51-acre lot, The Birdhouse delivers an unrivaled combination of character, sophistication, and downtown living. Originally built in 1920, this meticulously restored home preserves its historic charm through exposed brick walls, wood-beamed ceilings, vintage glass doorknobs, original lighting fixtures, multiple fireplaces, beautifully maintained hardwood floors and more. Natural light pours through original diamond-pane windows into the spacious family room, while the formal living and dining rooms showcase timeless character and thoughtful custom details. The chef's kitchen is a true focal point with a distinctive mix of old-world charm and modern design that combine luxury and function. Features include Cambria Portrush quartz countertops, custom floor-to-ceiling cabinetry, premium ZLINE appliances with an 8 burner gas stove range below exposed brick walls, a statement tile backsplash and custom range hood. Floating wood shelves, an expansive breakfast bar and cozy breakfast nook with built-in seating complete its design. A spacious mudroom and custom laundry room offer extensive cabinetry and counterspace for both storage and everyday convenience and a dedicated home office includes a custom built in desk. Set apart from the living areas and secondary bedrooms, the newly designed primary suite serves as a private sanctuary. Accessed through its own hallway, this spacious retreat features vaulted wood-paneled ceilings, an enormous walk-in closet, and a spa-inspired bath with dual vanities, two private water closets, a large glass-enclosed shower and elevated finishes throughout. Four additional generously sized bedrooms provide exceptional flexibility, including a second primary suite with dual closets and an ensuite bath, an additional ensuite bedroom overlooking the pool, and two bedrooms with a full guest bath positioned in between. The enormous fully fenced backyard is designed for year round enjoyment with a gas-heated saltwater sport pool, outdoor kitchen, expansive brick paved deck, detached covered lanai, and low-maintenance turf. Towering above it all is one of the property's most extraordinary features: a majestic 390-year-old oak tree, recognized as the oldest recorded oak tree in Orange County, providing unparalleled beauty and shade. Equally noteworthy, the home's original exterior waterspout remains in place and fully operational, offering a unique connection to the property's storied past. A double carport includes both a Tesla and golf cart charging station as well as a large storage closet equipped with power and a shop desk. Recent home improvements include a new roof (May 2026), updated PVC plumbing and drain field, new air handler, new tankless hot water heater, new water filtration system and new structural support trusses installed beneath the home to enhance long-term stability and strengthen the property's foundation for generations to come. A rare blend of historic significance, modern luxury, and premier location, The Birdhouse represents one of Downtown Winter Garden's most exceptional residential offerings. Schedule your private viewing today!

234 N Lakeview Avenue, Winter Garden

$965,000

4 Beds ⋅ 3 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code

Welcome to a piece of history, right in the Winter Garden's golf cart district! This stunning Craftsman bungalow is nestled in the Historic District, where timeless character meets extensive modern updates. Set on a 0.34-acre lot beneath grandfather oaks, this home creates an atmosphere that feels peaceful while placing you just steps from the energy of downtown. From the moment you arrive, you're greeted by a gravel driveway(2021) that leads to the front of the property, while outdoor lighting (2021) creates a welcoming glow as the sun goes down. Step through the beautiful leaded glass front door into a home filled with warmth and character. Rich heart pine floors, 9-foot ceilings, and crown molding create a timeless backdrop that is sure to make everyone feel at home.The front living and dining area provides a comfortable place to entertain or settle in with loved ones. Nearby, a flexible room can function as a bedroom or home office, and includes its own half bath, giving you the freedom to shape the space around your family's needs. At the center of the home, the farmhouse-inspired kitchen includes real wood cabinetry, granite countertops, and a convenient side entry to make everything from everyday cooking to hosting dinners feel effortless. The side entrance also makes bringing in groceries especially convenient. Down the hall, two bedrooms create comfortable retreats and share a guest bathroom with subway tile detailing. The guest bathroom tub drain line was replaced in 2025, while extensive flooring and subfloor improvements completed throughout the home provide a refreshed foundation from room to room. Upstairs, you’ll find the new flooring that was installed in 2025, along with recessed lighting (2018), and a bright and inviting loft space with flexibility for a reading area or home office. The primary bedroom was remodeled in 2025 and includes a custom built-in closet for exceptional organization. The upstairs bathroom was also remodeled in 2025, creating a beautifully updated space to begin and end your day. The home has received extensive upgrades, providing the new owners with peace of mind that this home was truly cared for. Upgrades include a downstairs HVAC system (2023), a replacement of the downstairs ductwork (2025), foundation support installed beneath the rear half of the home with concrete footers (2024), and a new water heater (2025). The home's exterior has been refreshed as well, including Artificial turf (2021) for easy upkeep, new exterior paint (Dec, 2024) and a new roof (2023). Heading outside, you're bound to love the private fenced in backyard space. Whether you're imagining weekend gatherings, letting little ones play, or simply enjoying a quiet afternoon outdoors, there's room to create the backyard you've always wanted. The detached 25' x 25' garage and workshop adds another layer of flexibility, complete with 100-amp electrical service. For a hobbyist, craftsman, or anyone who needs additional storage and workspace, this building can become whatever your lifestyle requires.This is a home with character you simply can't recreate, paired with the extensive updates and improvements. And perhaps best of all, you're living in the heart of Historic Downtown Winter Garden, where morning walks, farmers markets, local dining, shopping, live entertainment, and community events can become part of your daily routine. Don't wait on this amazing home, schedule your private showing TODAY!

128 N Highland Avenue, Winter Garden

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Orange County › Winter Garden › Cooper & Sewell Addition

Cooper & Sewell Addition, Winter Garden

Cooper & Sewell Addition is a neighborhood in Winter Garden, in the 34787 zip code, built most often in the 1920s. Homes are block and wood frame, predominantly single story. Most homes fall between about 1,300 and 3,000 square feet under air, and the median lot is roughly a quarter acre.

Most of Cooper & Sewell Addition carries no mandatory HOA.

What the homes are

Built Most often built in the 1920s (42% of homes), with homes from 1914 to 2025.
Construction Block and wood frame. Shingle roofs on 88% of homes.
Style Bungalow, Historical, Ranch. Predominantly single story.
Size Most homes fall between about 1,300 and 3,000 square feet under air.
Bedrooms Three bedrooms is the most common plan, then four.
Lot The median lot is roughly a quarter acre.
HOA Most of the neighborhood carries no mandatory HOA. Confirm on a specific parcel before relying on it.

Where Cooper & Sewell Addition is

Cooper & Sewell Addition, centered at 28.565881, -81.589971. Drag to explore.

Street level, inside the neighborhood. Drag to look around.

Drive times below are measured on the road network from the center of Cooper & Sewell Addition, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving to	Time	Miles
Downtown Orlando	27 min	17.4
Walt Disney World	29 min	21.1
Orlando International Airport	32 min	25.8
Universal Orlando	26 min	16.3

Public schools nearby

SLV High School 4 min, 0.6 mi
Dillard Street Elementary School 3 min, 0.8 mi
Maxey Elementary School 5 min, 1.6 mi
Tildenville Elementary School 4 min, 1.4 mi

Private schools nearby

Foundation Academy, Plant Street Campus 3 min, 0.5 mi

Parks and recreation

Dr. Bradford Memorial Park 4 min, 0.8 mi
Veterans Memorial Park 2 min, 0.6 mi
Maple Street Park 4 min, 0.7 mi
Newton Park 4 min, 0.9 mi

Groceries and errands

The Ancient Olive Gourmet of Winter Garden 3 min, 0.5 mi
Tea Bar 2 min, 0.3 mi
Tn Food & Grocery 3 min, 0.5 mi
D J Discount Market 4 min, 0.5 mi

Useful local links

Nearest is not the same as zoned. The schools above are the closest ones to Cooper & Sewell Addition by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Cooper & Sewell Addition actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 2 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated November 2026.

Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.

What homes sold for in Cooper & Sewell Addition

$907,500Median sale price

$432Median per square foot

46 daysMedian days to contract

2Homes sold in 12 months

Sale prices ran from $555,000 to $1,260,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

Price cuts and time to contract

Median days to go under contract. Shorter is better.

Never reduced 1 sale, closed at 98.2% of asking0 days

Reduced at least once 1 sale, closed at 97.3% of the reduced price93 days

Sellers who held their number went under contract in a median 0 days. Sellers who had to reduce took 93 days and still closed at 97.3% of their already reduced price, after a typical cut of $200,000.

How buyers paid

Cash 1 sale50%

Conventional 1 sale50%

Cash was 50% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.

Questions about a specific home in Cooper & Sewell Addition, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for Cooper & Sewell Addition in Winter Garden, Orange County, covering closed sales from 7 November 2025 through 2 November 2026, refreshed monthly and current as of November 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. One record was excluded as an off-market transfer rather than an open market sale. Data believed accurate but not guaranteed; listings and closings change daily.