$829,299Average Value$445Average Price per Sq Ft6Homes For Sale
Positively presidential
In the neighborhood of Oakdale, a walk through history is as simple as a stroll down the streets. Within this section of the almost 400-year-old Boston suburb of Dedham, residents pass multiple streets named after former U.S. presidents—from John Adams to James Madison and Abraham Lincoln to Ulysses S. Grant. “The streets are picturesque,” says Sarah Sally, real estate agent with Donahue Realty and longtime resident of the area. “They’re filled with homes that carry a real stateliness to them.” Considered the most densely populated neighborhood in the town of Dedham, Oakdale is a popular choice for reasons beyond its proximity to Boston—though being less than 20 miles from the city doesn’t hurt.
Adams St sign in Oakdale.
Lincoln St sign in Oakdale.
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Renowned local architecture means classic charm
Homes in the Oakdale neighborhood are classic constructions, with many originating in the early/mid-20th century. “Oakdale is well known for its Bailey houses,” says Sally. “There big, beautiful structures full of history.” Named after the famous Dedham architect Robert Morris Bailey, these homes were constructed for himself, relatives, and friends. Apart from these, the most common styles in the neighborhood are Colonials and Cape Cods. Being suburban in its makeup, lots in Oakdale are relatively spacious—with well-kept yards offering privacy that balances nicely with its highly walkable streets and series of connected sidewalks. Prices for a 3-bedroom home tend to range from $585,000 to $750,000—though the more historic Bailey homes and larger estates can go for much more. “Those homes for go $1 million to $2 million easily,” says Sally.
Oakdale has many single family homes throughout the neighborhood.
Single family home with lush greenery along in Oakdale.
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Take a tour of local history
During free time, residents can take a quick excursion to Fairbanks Park for some outdoor fun. “The facility is great,” Sally says. “They have baseball fields there, and a big playground, which is nice,” she added. In the winter months, those looking to celebrate the season can head to nearby Wigwam Pond for ice skating. In the summer, meanwhile, residents can visit Oakdale’s historic Endicott Estate. This massive, 25-room Colonial-style home was constructed in 1904 by the founder of the former Endicott-Johnson Shoe Corporation, Henry Bradford Endicott. Now, Dedham hosts summer concerts on the lawn here. The home can also be rented for weddings and other events. The estate’s carriage house is now home to the Endicott branch of the Dedham Public Library.
Fairbanks open green space in Oakdale.
Endicott Estate building mainly used as a wedding venue and events in Oakdale.
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Stay close or head to Boston
Those looking for a bite to eat can grab food at the popular Yard House, a local chain with classic burgers and chicken nachos. Right next door to the Legacy Place shopping center, residents can pick up groceries for a home-cooked meal at the Whole Foods or Costco. Thanks to the proximity of Boston, residents also always have the option to head into the city for their favorite chain retailers or unique urban boutiques.
Yard House restaurant has outdoor seating in Oakdale.
Stop by the local Whole Foods Market in Oakdale for your grocery needs.
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Success at soccer and more at Dedham High
Students in the neighborhood start their learning at Oakdale Elementary, before moving on to Dedham Middle School and finishing up at Dedham High School. According to Niche, these schools earned grades of B-plus, B, and A-minus, respectively. Soccer is particularly successful at Dedham High, with both the boys and girls varsity teams making the state championship in 2022.
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Residents and visitors in Oakdale have easy access to the rail train station in Oakdale.
Commuting made easy in Oakdale
Oakdale’s desirability stems from not just the attractiveness of the homes’ architecture, but also the neighborhood’s proximity to the commuter rail, to schools and to the City of Boston. Oakdale borders Boston’s southernmost neighborhoods, in fact, and its residents are near both the Dedham Corporate Center and Endicott Massachusetts Bay Transportation Authority commuter rail stations. The trains that traverse both of these stops can have residents in Downtown Boston in about a half an hour.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Are you familiar with the Oakdale neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Oakdale
US
Homicide
3
4
Sexual Assault
2
4
Assault with Weapon
3
4
Robbery
3
4
Burglary
4
4
Motor Vehicle Theft
3
4
Larceny
3
4
Crime Score
2
4
Source: WhatIsMyCrimeRisk.com
Oakdale Demographics and Home Trends
On average, homes in Oakdale, Dedham sell after 21 days on the market compared to the national average of 55 days. The median sale price for homes in Oakdale, Dedham over the last 12 months is $805,000, up 8% from the median home sale price over the previous 12 months.
Located in the highly desirable Oakdale area, this picture-perfect Cape offers 3–4 bedrooms, 2 full baths, and exceptional value for the neighborhood. The first floor features an open-concept kitchen that flows seamlessly into a warm and inviting fireplaced living/dining area, creating the perfect space for entertaining or everyday. A flexible den or optional fourth bedroom, a separate living
ASK ABOUT QUALIFYING FOR 1% DOWN. RATES 5% & 10% DOWN PAYMENTS UNDER $3,000/MO INCLUDING HOA FEES. This attractive condominium awaits, presented in great condition. Within this residence, the kitchen stands as a testament to thoughtful design, featuring elegant stone countertops and classic shaker cabinets, perfectly integrated with a built-in refrigerator for a seamless aesthetic. This space
Welcome to 442 High Street, Dedham, MA – a fully renovated 3-bed, 4-bath W/ office. classic New England home that feels brand new in 2026 This move-in-ready gem offers 2,900 sq ft of thoughtfully designed space with gleaming refinished hardwood floors, an open concept living/dining area, and a stunning chef’s kitchen featuring quartz counters, white shaker cabinets, a large island, and stainless
Welcome home to this completely renovated and move-in ready 1-bedroom condo at 90 High Street, Unit 309 in Dedham. This beautifully updated unit offers modern comfort and convenience with brand-new luxury vinyl plank flooring, fresh paint throughout, and a stylish refreshed interior. The updated kitchen features upgraded cabinetry, countertops, and modern lighting, perfect for everyday living.
Rare offering: Large two-family property located in Oakdale Square. Spacious owners unit includes 2 Bedrooms one bathroom with hardwood floors, recessed lighting, multiple fire-places and large family room. Unit 2 is currently tenant-occupied; buyer to perform due diligence regarding tenancy. Property to be sold as-is.
Beautifully renovated single-family home located in a desirable residential setting in Dedham, MA. This spacious property features three bedrooms and one and a half bathrooms across over 2,000 square feet of living space. The home has been completely redone and is move-in ready with updated finishes throughout. The newly renovated kitchen includes stainless steel appliances, modern cabinetry, and
Extra spacious (more than 3,000 sq'), well maintained two family home located in convenient location within walking distance to Dedham Sq, bus stop, shopping, restaurants and more! Unit 1 features 5 big rooms including an oversized living room, dining room, eat-in kitchen, 2 king sized bedrooms and a full bath. Unit 2 features a big living room, family room, eat-in kitchen 2 good king sized
Desired Endicott location introduces you to this stately tudor style home combining old world charm with many updates for today's conveniences. From the front entry vestibule to the sweeping staircases, detailed woodwork, stain glass and high ceilings you are warmly welcomed. There are three finished floors of living space offering great flow. Fireplaced front sitting room and den are great
Our captivating location embodies a sociable atmosphere, within a 3 minute walk of Legacy Place offering the best shopping, dining and entertainment experience in the region. Take in the day with some of the trendiest boutique shops or experience the lavish collection of specialty retailers. Enjoy a dinner with friends at The Yard House and complete your evening at the Showcase Cinema De Lux or
Furnished one bedroom apartment located on the second floor in a majestic 6-unit Queen Anne Victorian. Gleaming hardwood floors throughout the unit with plenty of light in the living room. Extra-large master bedroom contains a new ceiling fan and clothes closet. Small den also has a small storage closet. Tiled eat-in kitchen with granite countertops, refrigerator, gas stove, and garbage disposal.
Live carefree every day. At The Avens at Dedham Station, coming home feels like you're on vacation. With impressive finishes and resort-quality amenities, our one-, two-, and three-bedroom apartments make it possible to live beyond your expectations. With so much to do in the perfect location, a vibrant new lifestyle awaits. Conveniently located next to premier shopping and dining at Legacy
AVAILABLE NOW ~ Brand New Construction! Dior Dedham is a newly constructed building with all of the amenities you could ask for. Conveniently located on Providence Highway, Residence at The Dior is a new construction building with four stories, great light and premium features in a prime Dedham location. You'll love the open concept floor plan and luxury finishes! This 2 Bedroom 2 Bath features:
Second floor furnished one bedroom to rent, 650 sq.ft, living room, kitchen, master bedroom, and washer/dryer. Commuters dream, short walk to Endicott & Dedham Corporate stops. A short drive to I-95 and Legacy Place! Located in desirable Endicott area, $2,500 a month which includes heat, hot water, snow removal, grounds maintenance and parking. First, Last, months rent and Security Deposit. No
AVAILABLE NOW! Dior Dedham is a newly constructed building with all of the amenities you could ask for. Conveniently located on Providence Highway, The Dior has 4 stories, Garage Parking, great light and premium features in a prime Dedham location. You'll love the open concept floor plan and luxury finishes! This 1 Bedroom 1 Bath features: - Open Concept Kitchen / Living area - Stainless Steel
Spacious 3-bedroom, 1-bathroom first-floor unit for rent in Dedham’s Oakdale area.Features hardwood floors throughout, an updated kitchen and bathroom, gas heating, and in-unit washer and dryer. Bright and comfortable living space.Rent includes heat, hot water, electricity, and water.No broker fee.Move-in costs: first month’s rent and one month security deposit.Conveniently located near Readville
Newly RENOVATED third-floor apartment located in the heart of Dedham’s desirable Oakdale neighborhood. This updated 2-bedroom, 1-bath unit features modern finishes and thoughtful upgrades throughout. Bonus additional office/den. Enjoy a brand-new kitchen with stainless steel appliances, gas stove, and dishwasher, plus a fully renovated bathroom with contemporary fixtures. The apartment offers new
Rare opportunity in Oakdale! This oversized half-duplex sits on a quiet, tree-lined street just steps from Oakdale Square. Brimming with charm and generous living space, the home features 4 bedrooms, 1.5 baths, a large living room, formal dining room, and a spacious kitchen. Enjoy 9-foot ceilings, oversized rooms, and hardwood floors throughout. Additional perks include a private driveway and a
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