Highland Real Estate

Highland is a hamlet of Ulster County located along route 9W. Part of the town of Lloyd, Highland sits along the west bank of the Hudson River just across from Poughkeepsie and has about 5,600 residents. This bustling hamlet is largely residential with a tractor supply store, supermarket, restaurants, and its own middle and high schools. The Hudson Valley Rail Trail is a favorite among locals, its entrance right in the middle of Highland. Take the trail east and it turns into the Walkway over the Hudson River, where you get sweeping views of the river and farmland. Illinois Mountain Park and Franny Reese State Park both fall within Highland as well.

The property for sale in Highland ranges from pricey land plots to more affordable single family homes, plus many commercial opportunities. The homes range from renovated farmhouses to Colonials and usually have a good-sized yard to boot.

Below, browse all real estate available in Highland

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139 Crow Hill Road Highland NY 12528

Highland, NY139 Crow Hill Road

Price$2,499,000

Est. Mortgage: $/month

MLS Number 20203373

  • Land Agricultural
  • MlsStatus ACTIVE
  • Address 139 Crow Hill Road

Privacy, Privacy, Privacy! Create a family compound in an idyllic setting for your family for generations to come, surrounded by mountain vistas, ridgeline views, your own private lakes, and your personal apple orchard near upscale New Paltz, New York. This blissful executive property has numerous buildable spots, all with magnificent Hudson Valley views. Located just 90 minutes from New York City, this gorgeous spot is in its own world in the heart of Ulster County apple country. Enjoy the rural life yet not be far from shopping, great restaurants, bars, a college atmosphere (SUNY New Paltz), and just minutes off the New York Thruway, exit 18, New Paltz. At 140 acres, this exquisite property has approximately 7,000 existing mature apple trees and a classic red barn dating back to 1840. Nestled in a bowl shape on the other side of the ridge from Apple Greens Golf Course (holes 19-27), this property features two private, interconnected, spring-fed lakes: 5+ acres of deep lakes with good groundwater. Property has its own private gravel road, which was the public road through the area from colonial times to the 1950s. And the views… ridgeline, cliffs, Catskill mountain range, surrounded by thousands of trees, and a spectacular view of Mohonk Fire Tower. This area is heaven for climbers, golfers, skiers, lovers of nature, and anyone who wants to go at a slower pace. You'll build your evening around catching the sunset up here, all the while a short drive or train ride into the city. Buildable for multiple houses, the purchaser retains the option to continue as an operational farm. Existing worker housing can be used, improved, or removed at buyer's option. There's 70 acres of apples trees with approximately 100 trees per acre. The property is served by the local electric utility (Central Hudson), landline phone/DSL company (Verizon) , and high speed internet/cable company (Spectrum). Must be seen to be believed! This kind of property brings family together, where generations can stay in one place and not be on top of each other. It's all about family, beautiful land, and privacy. Tax records show 107 acres but the deed state there are 140 acres. Property also includes Tax ID 513200.087.003-0005-016/0000. Cost per acre is actually $17,850.00 per acre.

Listed by Frank Tangredi, Frank Tangredi Realty Company

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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690 New Paltz Road Highland NY 12528

Highland, NY690 New Paltz Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 20212504

  • Residential Single Family
  • Square Feet 4,822
  • Lfd Style FARM HOUSE
  • Property Style Farm House
  • MlsStatus ACTIVE

Picture-perfect farm - bring your imagination to this 14.5 acre property's endless possibilities! This secluded farmhouse faces Southeast and was given a contemporary addition expanding it to 4,822 square feet. The heart of the residence is a double height living room with magnificent stone fireplace. The great room is impressive with floor to ceiling windows looking toward the classic Dutch barn; a state of the art chef's kitchen including Kraft-Maid cabinets with CaesarStone countertops, cooking show-worthy island, two Franke sinks, 36-inch cook-top, double wall ovens, dishwasher, under counter microwave drawer and professional built-in refrigerator and freezer. There's also a wine fridge and abundant storage. Relax on the wrap-around deck or on the screened porch. In the airy dining room there's a second wine fridge and bar, as well as beamed ceilings and a sliding barn door. The first floor also has a foyer, half bath and cheerful windowed laundry room. Up the original farmhouse stairs are four bedrooms and a large hallway bath. The primary bedroom has a spacious en-suite bathroom with soaking tub and separate shower. There's a skylit one-bedroom access apartment with private entrance and plenty of closet space. This could also be used as an office suite. The acreage is complete with twin spring-fed streams, pond, riding paddocks, pastures, a splendid 18th-century Dutch barn, 14 stall stable, stone smokehouse, tree house, chicken coop, and stone well house. The smaller 1,300 square foot bridle barn is currently a shop, licensed under NYS agriculture and markets, with an office space on the second floor. The antique hand-hewn timber has been preserved, and high-speed Internet, heat and air-conditioning have been added. This charmer has an adjoining garden with raised beds and fruit trees. The property can be self-sustainable. It would also make a wonderful home or weekend getaway. Discover a winning combination of work/life balance, and make your dreams of country life come true.

Listed by Veronica Newton, Compass Greater New York,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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17 Cross Creek Run Highland NY 12528

Highland, NY17 Cross Creek Run

Price$1,250,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 20213842

  • Residential Single Family
  • Property Style Contempo
  • Square Feet 3,682
  • Address 17 Cross Creek Run
  • Year Built 1996

The Hudson Valley, a quiet and vibrant region with magnificent scenery, cultural treasures, farm-to-table cuisine, a robust art and music scene and epic outdoor adventures, was named the Top 20 Best of the World Destinations. This custom designed and built contemporary is no exception to the rule. Set on the west banks of the Hudson River, a picturesque tree-lined driveway will lead you to this truly stunning Adirondack style home with a cedar shake roof. A dramatic ten-mile view of the Hudson River offers complete privacy and seclusion, yet with the conveniences you are seeking in a full-time or weekend residence, just 15-minutes from the MetroNorth and NYS Thruway, and 90-miles north of Manhattan. This 3.3 acre property includes a quarter acre working vineyard growing pinot noir, riesling and viognier, a small lavender field, and charming country gardens. Hiking at the John Burroughs Nature Preserve and Black Creek Preserve are within three miles. Minnewaska State Park and the world-renowned Mohonk Preserve in the Shawangunk range is nearby offering hiking and rock climbing. Summers bring a variety of songbirds; bald eagles soar past daily year-round; Hudson River wildlife is in abundance. The architecturally designed home features an open concept design with spacious living spaces, sun-drenched natural light, clean lines and dramatic custom windows overlooking the river. Four bedrooms, three and a half baths, two work-from-home office spaces, a temperature-controlled wine room, an unfinished basement with eleven-foot ceilings suitable for a studio, and a cantilevered back deck overlooking the Hudson. Off the master bedroom is a porch that overlooks a hemlock grove and a small creek running to the river. Experience the true splendor of the Hudson Valley in this unique home.

Listed by Lindsay Stevens, eXp Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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50 John White Highland NY 12528

Highland, NY50 John White

Price$895,000

Est. Mortgage: $/month

MLS Number 20211964

  • Residential Single Family
  • MlsStatus ACTIVE
  • Square Feet 1,560
  • Lfd Style RANCH, TWO STORY
  • Property Style Ranch

FABULOUS & UNIQUE INVESTMENT OPPORTUNITY!!! "Privacy" If you are looking for a beautiful, quiet secluded property this is a must see. Situated on 16.4 acres. This can be a NICE get away which includes income property nestled at the end of John White Rd. The main house has 3 bedrooms and 2 baths with hardwood floors throughout with all new appliances. The second home is a 3 FAMILY farm house built in 1873 that has been re-done over the years, All with with 2 bedrooms and 1 bath each. All 3 units are and have been successfully rented for many years. This Parcel also includes a VINTAGE BARN that does need some TLC but can totally be used for some farm animals, or anything that you would like. This property has endless possibilities and is also sub-dividable. There is a extra 2.9 acre parcel which is an adjacent lot that has rd frontage to Riverside Rd & John White Rd which can be made into an access rd. All of this is just minutes away from Mid Hudson Bridge, The Walkway over the Hudson and NYS Thruway. Don't miss out on this great property/retreat.

Listed by Angela Chenery, Keller Williams Realty HV Nort

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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50 John White Road Highland NY 12528

Highland, NY50 John White Road

Price$895,000

Est. Mortgage: $/month

MLS Number 20211965

  • MultiFamily 4 Family
  • MlsStatus ACTIVE
  • Address 50 John White Road
  • Year Built 1873

FABULOUS & UNIQUE INVESTMENT OPPORTUNITY!!! "Privacy" If you are looking for a beautiful, quiet secluded property this is a must see. Situated on 16.4 acres. This can be a NICE get away which includes income property nestled at the end of John White Rd. The main house has 3 bedrooms and 2 baths with hardwood floors throughout with all new appliances. The second home is a 3 FAMILY farm house built in 1873 that has been re-done over the years,All with with 2 bedrooms and 1 bath each. All 3 units are and have been successfully rented for many years. This Parcel also includes a VINTAGE BARN that does need some TLC but can totally be used for some farm animals, or anything that you would like. This property has endless possibilities and is also sub-dividable. There is a extra 2.9 acre parcel which is an adjacent lot that has rd frontage to Riverside Rd & John White Rd which can be made into an access rd. All of this is just minutes away from Mid Hudson Bridge, The Walkway over the Hudson and NYS Thruway. Don't miss out on this great property/retreat.

Listed by Angela Chenery, Keller Williams Realty HV Nort

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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430 N Riverside Highland NY 12528

Highland, NY430 N Riverside

Price$890,000

Est. Mortgage: $/month

MLS Number 20210474

  • Residential Single Family
  • Lfd Style CONTEMPO
  • MlsStatus ACTIVE
  • Property Style Contempo
  • Square Feet 4,500

Hudson Valley living at its finest! Magnificent custom-built property privately situated down a long drive on 7.4 acres just minutes to the charming villages of Highland and New Paltz, miles of hiking, biking and cross-country skiing trails in the Shawangunk mountains or to the stunning views of the Walkway Over the Hudson or drop a kayak into Black Creek literally just across the way. This is just to name a few among so many of our local treasures easily accessible to this location. Currently operating as a successful Bed and Breakfast, you can live, work, and play in this premiere Hudson Valley location. The layout of this home offers complete privacy for the owners and their guests with multiple entrances. The great room features a magnificent fireplace and a wall of windows awash in natural light with pond views. All 5 luxuriously appointed guest rooms have their own private bath. Master bedroom suite with oversized spa like bathroom, private seating area, balcony and fireplace. Lower level features a 6 person hot tub and one of 3 of the homes fireplaces. There is room for expansion on lower level, currently used for storage. The pond is home to blue heron and ducks in warmer weather. And there are hiking trails on this beautifully wooded piece of land with rock outcroppings and a rock cave of archaeological significance worth exploring! Now a turnkey business, offered complete with contents, website, social media, guest list and advanced reservations. Owners have successfully met all Covid related CDC guidelines and have been operating safely and with quite a high demand, with people's increased need to escape tight urban quarters and step outside, even in this brisk winter, to snow shoe and ski. Spring, Summer and Fall months they enjoy the many surrounding open air restaurants, farm markets, wineries and breweries. Just 5 minutes to Exit 18 off NYS Thruway and 10 minutes to Metro-North station in Poughkeepsie, it really is the perfect location! This home was originally a single-family residence. Buyer would need to do nothing more than redecorate to make this once again a grand single-family home with room for everyone! The energy effeciency of this home has been expanded upon with the addition of geothermal heating and cooling as well individual mini-split units. Not pictured are an additional bedroom, living room and bath used by the owners. Available to view at showing. Please check out their website for more pictures and details. https://www.blackcreekbedandbreakfast.com/en/1429954/gallery

Listed by Victoria Beach, eXp Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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430 N Riverside Highland NY

MLS Number 20213291

  • Commercial Bed & Breakfast
  • MlsStatus ACTIVE
  • Square Feet 4,500
  • Address 430 N Riverside
  • Year Built 1985

Nestled right in the middle of all the wonderful things the area has to offer sits this fully operating, thriving, turn-key, Bed and Breakfast. Magnificent custom-built property privately situated down a long drive on 7.4 acres just minutes to the charming villages of Highland and New Paltz, miles of hiking, biking and cross-country skiing on the trails of Mohonk Preserve, Minnewaska State Park, the Empire State Park and the stunning views of the Walkway Over the Hudson or drop a kayak into Black Creek literally just across the way. This is just to name a few among so many of our local treasures, easily accessible to this location. Currently operating as a successful Bed and Breakfast, you can live, work, and play in this premiere Hudson Valley location. The layout of this home offers complete privacy for the owners and their guests with multiple entrances. The great room features a magnificent fireplace and a wall of windows awash in natural light with pond views. All 5 luxuriously appointed guestrooms have their own private bath. Master bedroom suite with oversized spa like bathroom, private seating area, balcony and fireplace. Lower level features a 6 person hot tub and one of 3 of the homes fireplaces. There is room for expansion on lower level, currently used for storage. The pond is home to blue heron and ducks in warmer weather. And there are hiking trails on this beautifully wooded piece of land with rock outcroppings and a rock cave of archaeological significance worth exploring! A turnkey business, offered complete with contents, branding, website, social media presence, guest list and advanced reservations. Owners have successfully met all Covid related CDC guidelines and have been operating safely and at high demand, with people's increased need to escape tight urban quarters and step outside. Fall is amazing in the Hudson Valley! And even a brisk winter, lends itself to local snow shoeing and x-country skiing. Enjoy the many surrounding open air restaurants, farm markets, wineries, breweries and distilleries. Just 5 minutes to Exit 18 off NYS Thruway and 10 minutes to Metro-North station in Poughkeepsie, it really is the perfect location! The energy efficiency of this home has been expanded upon with the addition of geothermal heating and cooling, as well individual mini-split units. Not pictured are an additional bedroom, living room and bath used by the owners. Available to view at showing. It's a great vacation spot and business is booming! Come find your life, work balance here in the beautiful Hudson Valley!!! https://www.blackcreekbedandbreakfast.com/

Listed by Victoria Beach, eXp Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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tbd South Street Highland NY 12528

Highland, NYtbd South Street

Price$850,000

Est. Mortgage: $/month

MLS Number 20204655

  • Land Agricultural
  • MlsStatus ACTIVE
  • Address tbd South Street

Approvals are nearing completion for 9 lot subdivision. Cluster development. Perfect for upscale homes. Developer, Builder, or Architect, ATTENTION! This acreage is waiting for your dream house or dream development of homes with GOLF COURSE next door and panoramic views of mountains and valley. Picture your home owners riding to the course on a golf cart! Mountain Views. Country living.

Listed by Andre Venables, Century 21 Alliance-NP

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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346 Crescent Avenue Highland NY 12528

Highland, NY346 Crescent Avenue

Price$845,000

Est. Mortgage: $/month

MLS Number 20213835

  • Residential 1Family+Access Apt
  • Lfd Style FARM HOUSE
  • MlsStatus ACTIVE
  • Property Style Farm House
  • Square Feet 6,406

The Historic 'Clintondale Elixir Spring House' is a rare offering to the market. Built in 1790 and with 6,400+ sq ft of living space, whether this becomes your forever home, there is so much to love and discover about this residence. Enter the main farm house from the charming rocking chair front porch into a grand foyer with a cathedral ceiling, where a cherry wood staircase with a balcony connects two levels of living. For intimate affairs, there is a formal dining room and a formal living room with exposed bluestone walls, wide-plank floors and dramatic beamed ceilings. The original cooking fireplace, set behind a brick wall, is waiting for you to return it to its original splendor, well worth the effort to be restored. Also on the main level the gourmet eat-in kitchen features gas cooking and lots of natural light. Upstairs, four bedrooms await, including three with their own full bath. A walk-up attic exudes architectural character with a high ceiling and a full floor, ready to be converted into anything you need whether that's extra storage space or a living area. In the Addition you will find a fitness/yoga studio with it's private entrance to ensure added flexibility. On the first and second floor are two 1-bedroom spaces, each with a private entrance. Further located on the third floor there are eight additional bedrooms, some connected and with their own in-room sink, all with access to one of the two full baths and two half baths. Start your day with a coffee in hand as you enjoy the manicured lawns and gorgeous trees as well as an antique four-stall outhouse, that creates a sense of a bygone era, from the comfort of the rear patio. Centrally located near New Paltz, NYS Thruway, and only 86 miles from NYC, this quiet country setting is conveniently located close to Mohonk Mountain, Lake Minnewaska, Dia Beacon, Storm King, Walkway Over The Hudson, Buttermilk Falls or the mansions that line the Hudson. Fine dining and shopping are all within easy reach. This is a rare find! There is nothing like this on the market right now.

Listed by Mario Geissler, Halter Associates Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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346 Crescent Avenue Highland NY 12528

Highland, NY346 Crescent Avenue

Price$845,000

Est. Mortgage: $/month

MLS Number 20213836

  • Residential Single Family
  • Lfd Style FARM HOUSE
  • MlsStatus ACTIVE
  • Property Style Farm House
  • Square Feet 6,406

The Historic 'Clintondale Elixir Spring House' is a rare offering to the market. Built in 1790 and with 6,400+ sq ft of living space, whether this becomes your forever home, there is so much to love and discover about this residence. Enter the main farm house from the charming rocking chair front porch into a grand foyer with a cathedral ceiling, where a cherry wood staircase with a balcony connects two levels of living. For intimate affairs, there is a formal dining room and a formal living room with exposed bluestone walls, wide-plank floors and dramatic beamed ceilings. The original cooking fireplace, set behind a brick wall, is waiting for you to return it to its original splendor, well worth the effort to be restored. Also on the main level the gourmet eat-in kitchen features gas cooking and lots of natural light. Upstairs, four bedrooms await, including three with their own full bath. A walk-up attic exudes architectural character with a high ceiling and a full floor, ready to be converted into anything you need whether that's extra storage space or a living area. In the Addition you will find a fitness/yoga studio with it's private entrance to ensure added flexibility. On the first and second floor are two 1-bedroom spaces, each with a private entrance. Further located on the third floor there are eight additional bedrooms, some connected and with their own in-room sink, all with access to one of the two full baths and two half baths. Start your day with a coffee in hand as you enjoy the manicured lawns and gorgeous trees as well as an antique four-stall outhouse, that creates a sense of a bygone era, from the comfort of the rear patio. Centrally located near New Paltz, NYS Thruway, and only 86 miles from NYC, this quiet country setting is conveniently located close to Mohonk Mountain, Lake Minnewaska, Dia Beacon, Storm King, Walkway Over The Hudson, Buttermilk Falls or the mansions that line the Hudson. Fine dining and shopping are all within easy reach. This is a rare find! There is nothing like this on the market right now.

Listed by Mario Geissler, Halter Associates Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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330 Plutarch Road Highland NY 12528

Highland, NY330 Plutarch Road

Price$725,000

Est. Mortgage: $/month

MLS Number 20181549

  • Land Residential
  • MlsStatus ACTIVE
  • Address 330 Plutarch Road

Beautiful 78.7 acre parcel located on west side of Plutarch Road in Town of New Paltz. With over 1000 feet of Road frontage the property is well suited for development. Included in the sale is an adorable English style stone cottage , one bedroom and large loft area. Hardwood floors throughout. Gorgeous stone walls meander through the undulating terrain. This property is a must see- very unique and so well located. Minutes from New York State Thruway, Metro North, the Gunks and not to mention our beautiful Walkway and Railtrail.

Listed by Marilyn De Angelo, Win Morrison Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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230-234 Vineyard Avenue Highland NY 12528

Highland, NY230-234 Vineyard Avenue

Price$720,000

Est. Mortgage: $/month

MLS Number 20205272

  • MultiFamily Multi-Unit
  • MlsStatus ACTIVE
  • Style DUPLEX
  • Year Built 1986

First time available in almost 30 years! These three duplexes, on three contiguous lots, are being sold as a package. The three lots currently generate over $60K in annual revenue combined. Each property contains a duplex with two 2-bed units. Instant cashflow or renovate for potential rent increases. Homes sold as-is. Additional revenue opportunity through coin operated laundry machines (not currently present). Seller financing can be negotiated. Just one mile to shops, restaurants and cafes along the main strip in Highland. Don't miss out on this opportunity!

Listed by Lindsay Stevens, eXp Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details