Heather Osgood

Bend OR

Windermere Realty Trust

10 Closed Sales

$4.9M Total Value

$90K - $930K Price Range

$487.1K Average Price

Prior five years

About Heather

Luxury Real Estate Broker | Equestrian Property Specialist | 20+ Years Serving Oregon & Washington | Trusted Referral Partner Nationwide

Heather Osgood is a fourth-generation Real Estate Broker with 20+ years of experience representing luxury homes, equestrian estates, resort properties, and new home developments throughout Oregon and Washington.

A Central Oregon native, raised in Sisters, Heather combines deep regional insight with a lifelong passion for the equestrian lifestyle. Her unique background and proven marketing expertise have made her a trusted partner for discerning buyers and sellers seeking exceptional service and results.

She has a solid referral network and thrives on matching clients with exceptional professionals around the country and beyond. Heather is known for her integrity, market knowledge, and commitment to delivering a seamless and successful real estate experience.

Licensed with Windermere in Oregon and Washington.

Home Types: Manufactured, House, Lot/Land

Years of Experience: 29

Transaction History

1 Year
2 Year

Seller Deals

Total Deals

Total Value

$2,112,800

Average Sale Price

$352,133

Price Range

$90K - $519K

Buyer Deals

Total Deals

Total Value

$1,149,400

Average Sale Price

$574,700

Price Range

$500K - $650K

Seller Deals

Total Deals

Total Value

$2,112,800

Average Sale Price

$352,133

Price Range

$90K - $519K

Buyer Deals

Total Deals

Total Value

$1,828,400

Average Sale Price

$609,467

Price Range

$500K - $679K

Neighborhoods Heather is Experienced In

Redmond

4 Sales
Mountain View

1 Sale
Boyd Acres

1 Sale

Heather's Open Houses

$1,425,000 Open Sat 12PM - 2PM
- 3 Beds
- 3.5 Baths
- 3,186 Sq Ft
2279 NW Putnam Rd

Bend, OR
Stunning custom Spanish-style home in Bend's desirable Awbrey Glen golf community. Built by a master cabinet maker, this home features exquisite cherry and exotic hardwood throughout, Rastra ICF construction, and soaring 16' ceilings. The gourmet kitchen offers a large wraparound bar, granite countertops, crushed granite sink, and abundant cabinetry. Main level includes two spacious primary

Heather Osgood Windermere Realty Trust

Heather's Active Listings

$1,250,000
- 3 Beds
- 2 Baths
- 1,359 Sq Ft
2640 NE 8th St

Bend, OR
Development opportunity in an established neighborhood, near Hollinshead Park, medical, commute access and Bend amenities. 1.13 acres offers many options and a preliminary plan is available. Adjacent properties are available including 2667 NE Jones Rd (MLS220201590) Please contact listing agent for a complete packet of information and more details.

Heather Osgood Windermere Realty Trust

$999,950
- 4 Beds
- 3 Baths
- 3,330 Sq Ft
25480 Bachelor Ln

Bend, OR
This newly completed single-level home offers the ideal combination of privacy, flexibility, and lifestyle. Set on 4.4 acres at the end of a quiet country lane, it provides room to breathe and space to personalize. The thoughtful, versatile floor plan easily accommodates multigenerational living, guest quarters, or dedicated areas for work and hobbies. Two oversized garages with workshop space

Heather Osgood Windermere Realty Trust

$1,950,000
- 2 Beds
- 2 Baths
- 2,187 Sq Ft
22500 Alfalfa Market Rd

Bend, OR
Imagine waking up to the sound of horses and the open skies, just minutes from Bend. Bordering BLM land for endless trail access, this 19.72-acre ranch features panoramic mtn views and thoughtfully designed layout for both private enjoyment and professional use. Multiple barns, 20+ run-in stalls, 14 dry lots and irrigated pasture turnouts. Expansive 120x80 indoor arena, complete with 8 stalls,

Heather Osgood Windermere Realty Trust

$779,000
- 3 Beds
- 2 Baths
- 1,392 Sq Ft
25601 SW Suttle-Sherman Rd

Camp Sherman, OR
Check out the fresh stain and paint, plus incredible fall colors! An unrivaled location and deeded property and land which means no limits on your ownership, enjoyment and use. Not USFS, No HOA and Not part of a resort. Mere minutes from world-class flyfishing on the Metolius River, plus the Camp Sherman Store and Hola Restaurant. Charming 3 bedroom, 2 bath cabin offers a vaulted great room with

Heather Osgood Windermere Realty Trust

$600,000
- 2 Beds
- 1 Bath
- 960 Sq Ft
2667 NE Jones Rd

Bend, OR
Attn Developers - this .25ac property is located adjacent to 2640 NE 8th (MLS 220201390) making this a superb development opportunity. Established NE neighborhood, near Hollinshead Park, medical, commute access and Bend amenities. Please contact listing agent for a complete packet of information and more details.

Heather Osgood Windermere Realty Trust

$1,999,999
- 3 Beds
- 4 Baths
- 3,016 Sq Ft
19190 Pinehurst Rd

Bend, OR
Discover 58.55 acres in the heart of Tumalo, where sweeping Cascade Mountain views set the backdrop for endless possibilities. Whether your vision is an expansive private estate, a premier equestrian facility, or productive farmland, this exceptional property offers a remarkable canvas. Currently home to a hunting dog operation, the land features 39.21 acres of TID irrigation (portion in

Heather Osgood Windermere Realty Trust

$455,000
- 3 Beds
- 2.5 Baths
- 1,497 Sq Ft
20269 Schaeffer Dr

Bend, OR
Low-Maintenance Living in NW BendThis well-maintained townhome offers easy living with a bright, spacious interior and minimal upkeep. Inside, you'll find an open main level with abundant natural light and a cozy gas fireplace. Upstairs, a versatile loft is perfect for a home office, reading nook, or creative space.Thoughtfully designed for privacy, the home shares only a garage wall with

Heather Osgood Windermere Realty Trust

Awards and Designations

NAR - National Association of Realtors
GRI - Graduate REALTOR Institute
ABR - Accredited Buyer Representative

Other Experience

Investments, Luxury Homes, New Construction

Heather Osgood

(855) 416-4141

Heather Osgood

About Heather

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Neighborhoods Heather is Experienced In

Heather's Listings and Deals

Heather's Open Houses

Heather's Active Listings

Awards and Designations

Other Experience