$588,478Average Value$404Average Price per Sq Ft19Homes For Sale
Relics of the past below Ashokan High Point’s summit
Ashokan High Point’s 3,081-foot peak occupies about half of the Olive neighborhood in upstate New York, but there’s far more within its wooded slopes than initially meets the eye. Trails unfold under a canopy of foliage, leading to a summit ledge with a craggy drop below. “Essentially, the way that we always describe Olive is it's not that close to anything, but it is pretty close to a ton of things,” says Megan Brenn-White, the founder and CEO of the Upstate Curious Team. “It’s in this incredibly beautiful area essentially at the base of the Catskills, so you just kind of drive up to get there from almost anywhere and then you have these beautiful winding roads and views of the mountains.”
Three particular features distinguish it, making trips to High Point as much about the flora and fauna as it is about unique sights along the paths. Just off a portion of the trail, the jagged and skeletal remains of a World War II-era plane jut up from the ground vegetation. The cockpit and its framework are discernible among the mangled pieces of metal, a relic of a time long past. Along the journey up the mountain, hikers also find “cairn fields” consisting of stacks of stones believed to have been constructed thousands of years ago. The final significant feature of the landscape is the “Blind Lady’s House,” a stone-walled ruin lying among the trees.
Rolling forest hills can be seen all throughout Olive.
Residents of Olive can take hikes to Ashokan High Point.
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Hiking up the mountain or fishing at Ashokan Reservoir
A 9-mile trail winds its way up the slopes of Ashokan High Point to its summit, allowing for access to and viewing of the plane wreckage, other ruins and the cairn fields. The trailhead is located off Watson Hollow Road in the southwestern part of the neighborhood.
The mountain isn’t the only recreational outlet in the neighborhood. Parts of the Ashokan Reservoir occupy Olive’s northern region. Though swimming is prohibited in the body of water, seafarers take to the waves for unpowered boating and fishing. The Ashokan Quarry Trail is among the paths that wind around the reservoir’s outer edges, and visitors to Lester S. Davis Park play basketball and baseball or hop in the pool. The Sundown Wild Forest and other preserves are nearby, as well.
Take a stroll along the scenic Ashokan Reservoir in Olive.
Toss a line in and see what you can pull up in the waterways in Olive.
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Olive Day celebrates neighborhood history
The town of Olive puts on Olive Day to commemorate the town’s heritage from morning to evening on a Saturday each September. “Olive Day is so cute,” Brenn-White says. “It’s a really sweet annual festival. I've been there a few times. It's a super beautiful setting, because where they have Olive Day and where the Olive Public Library is, you're near the reservoir but you're seeing the huge Catskills. It's a really beautiful setting. It brings a lot of the people from the community together, and they have contests and stuff.”
It was established in 1823 and, as such, celebrated its 200th anniversary in 2023, but the bicentennial was far from the first time residents have paid homage to the neighborhood. Located at the Davis Park Pavilion off Watson Hollow Road, a frog jump and 5K race are among the event’s traditions. Attendees also take in live music, engage in crafts and more.
Longstanding inns and bars in Olive
The Country Inn and Petaly’s Restaurant is the most prominent eatery in southern Olive. It serves as a bed-and-breakfast and a three-day-a-week restaurant that seats patrons indoors and out, even hosting holiday events. In the northern part of the neighborhood, Route 28 is the site of multiple dining establishments, including the Boiceville Inn and its freshly-baked pizza. For more general shopping, residents head to a Hannaford just under 15 miles northeast in West Hurley or Target and Walmart locations in Kingston, over 20 miles east.
One of Olive’s most unique outlets is Snyder’s Tavern, situated along Route 28A on the south side of the reservoir. The beloved dive bar’s exterior is one of aging siding, overgrown foliage and a turret of Victorian sorts, and was a filming location for a forthcoming horror movie. "Snyder's Tavern 100% looks like an abandoned building from the outside,” Brenn-White says. “You cannot believe that it’s still open when you drive by.” Neon signs indicate the barroom atmosphere inside, which also consists of a jukebox and a pool table.
Snyder's Tavern is a local favorite of Olive residents.
The Country Inn Restaurant Market and B&B is a local neighborhood landmark of Olive.
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Architectural variety spaced throughout Olive
Properties in Olive are spaced out and architecture varies widely, from ranch-style homes and sprawling vintage farmhouses to Cape Cods and contemporary designs. “You have cabins with a lot of character, mid-century stuff, A-frames and a lot of beautiful, old farmhouses,” Brenn-White says. “There’s even some stone houses from the earliest days, when the Dutch and English settled here.”
Prices rarely drop below $300,000 and often span up to $750,000. Large farmhouses and other custom homes typically run from about $900,000 up into the million-dollar range. “This whole area, the Hudson Valley and the Catskills, have two parallel markets,” Brenn-White says, adding that the second-home market is driven by the area’s natural surroundings and distance from the city. “One is people who are earning their salaries here and live here full-time. the other are people who either are weekenders or they work remotely.”
Cabin style homes and more can be found in Olive.
Farmhouses, barns, and farm inspired homes can be found all around Olive.
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Three schools on the same campus in Olive
Kids from kindergarten through third grade attend Woodstock Elementary School, located less than 10 miles northeast of the neighborhood in the town of the same name and rated a B-plus by Niche. The Olive neighborhood is the site of the rest of students’ education, continuing at the B-minus-rated Reginald Bennett Elementary School. On the same campus as Bennett Elementary, Onteora Middle School and Onteora High School serve grades seven to eight and nine through 12, respectively. Onteora Middle gets a B-plus from Niche, while Onteora High receives an A-minus.
Onteora High School has 413 students 87% of which are at least proficient in math.
Onteora Middle School has 171 students of which 47% of students are proficient in reading.
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Route 28 splits the Ashokan Reservoir
New York State Route 28 traces its way along the north side of the reservoir. It splits at the west end to also become Route 28A on the reservoir’s south side before merging back into one road before it reaches nearby Kingston. Kingston itself is about 20 miles east from the center of Olive, and access to the New York State Thruway is around the same distance from the neighborhood. “We always tell people you have to go 20 minutes before you can start to get anywhere from Olive,” Brenn-White says, “because you often have to drive 20 minutes to get to 28 or Route 209.” The thruway links to Albany about 70 miles north, New York City over 100 miles south and other major areas in the state.
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
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Crime and Safety
1 - Low Crime, 10 - High Crime
Olive
US
Homicide
2
4
Sexual Assault
1
4
Assault with Weapon
1
4
Robbery
1
4
Burglary
2
4
Motor Vehicle Theft
2
4
Larceny
1
4
Crime Score
1
4
Source: WhatIsMyCrimeRisk.com
Olive Demographics and Home Trends
On average, homes in Olive, Shokan sell after 72 days on the market compared to the national average of 55 days. The median sale price for homes in Olive, Shokan over the last 12 months is $542,500, up 2% from the median home sale price over the previous 12 months.
Built in 2023 and set on over seven private acres, this stunning contemporary home delivers modern design, open space, and true Hudson Valley serenity. Soaring ceilings and a thoughtfully designed open floor plan fill the home with natural light, creating an atmosphere that is equally suited for peaceful everyday living and effortless entertaining. The sleek, modern kitchen flows seamlessly into
This property is conveniently located between Woodstock and Phoenicia, This stunning .90 acre, 3bed/2bath renovated 2-story home with both floors having an open floor plan with skylights on the 2nd floor, transom windows, and has beautiful wood accents. The second floor has high ceilings, skylights and loft-like great room that showcase picturesque sunsets and mountain views. The first floor open
Incredible 27.9-acre development opportunity with mixed-use zoning and dual access from Route 28 and Upper Boiceville road. The front portion is zoned Highway Business with a 0.5-acre minimum, ideal for commercial use along this high-traffic corridor. The rear is zoned residential with a 1-acre minimum and could be subdivided for housing, a strip along the middle can go either way to be added to
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Perched in a quiet Catskills setting, this 3.7-acre parcel offers a rare opportunity to create a private retreat with views of the Ashokan Reservoir--just waiting to be revealed with thoughtful clearing. Tucked behind your own wooded landscape surrounded by mountains ridges and peaks, the property delivers a true sense of seclusion while remaining remarkably close to everything that makes the
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Investor opportunity in Olivebridge! Situated on 1.12 acres, 106 Sheldon Hill Road offers a 2-bedroom, 1.5-bath home with approximately 1,456 square feet of living space and a full unfinished basement, providing additional potential for storage or future expansion. Ideal for investors, contractors, or buyers looking for a renovation project in the Hudson Valley, this home presents a chance to
You'll understand just how special this 41 Acre property is once you arrive. Just driving down the country road to get here is already a treat. Situated at the base of the majestic High Point Mountain you'll find a private driveway that takes you through a beautiful forest and then it opens up to acres of your own open farmlands.....the open fields are perfectly suited to horses and with an
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The perfect getaway from the hustle and bustle of the world. Nestled quietly in the Catskill Mountain Range, just minutes from the Ashokan Reservoir and a short drive away from Woodstock, Rosendale, Kingston, and New Paltz sits this lovely, renovated 2 bed, 1 bath home. On the property you'll find 2.2 acres of tranquility as you can look out the back windows at nearly all hours and see the
Welcome to 90 Jomar Lane, a spacious, move-in-ready ranch thoughtfully laid out for comfortable living. An additional 920 sq ft of living space is located in the fully finished basement and is not included in the 1,568 sq ft of the main level. This home features 3 bedrooms and 3 full bathrooms, and a large walk-up attic offering excellent storage or future potential. The primary bedroom opens to
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Stunning, very private,chateau style, 2 story seasonal rental in Olivebridge. It is inside the ''blue line''of Catskill State Park. Surrounded by over 22 acres this beautiful log home is perfect for anyone looking for a true getaway in the pines. Close proximity to the Ashokan Reservoir, skiing, hiking, wonderful restaurants and shopping. Fully furnished with gorgeous high ceilings, a wood
What an amazing place to spend the summer! Just 15 minutes from Woodstock and Phoenicia, you are right in the middle of all the Hudson Valley has to offer! Experience the rare opportunity to lease an extraordinary 70 acre estate where breathtaking natural beauty meets timeless sophistication.This reimagined three bedroom, 3 bath farmhouse blends rustic charm with refined modern luxury, creating a
This property is also listed as a summer rental with no equestrian facilities for 7500 a month.MLS# 20260328 Experience the rare opportunity to lease an extraordinary 70 acre equestrian estate where breathtaking natural beauty meets timeless sophistication.This reimagined three bedroom, 3 bath farmhouse blends rustic charm with refined modern luxury, creating a country life-style immersed in
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